2-((Methoxycarbonyl)amino)-3-methylbutanoic acid → HCID 66620428, compound

HRID 2392422Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:32])[NH:4][CH:5]([C:9]([N:11]1[CH2:15][CH2:14][CH2:13][CH:12]1[C:16](=O)[NH:17][C:18]1[CH:19]=C(C2C=CC(Cl)=CC=2)[CH:21]=[CH:22][CH:23]=1)=[O:10])C(C)C.C(OC(N1CCCC1C(=O)NC1C=[C:49]([C:53]2[CH:58]=[CH:57][C:56](Cl)=[CH:55][CH:54]=2)C=CC=1)=O)(C)(C)C.[C:61]([CH2:63]C(NC(OC)=O)C(O)=O)#[N:62].COC(N[CH:78](C(C)C)[C:79](O)=O)=O.COC(=O)[NH:88]C(C(N1CCCC1C1NC(C2C=CC(C3C=CC4C(=CC=C(C5NC(C6C7CC(CC7)N6C(=O)C(NC(OC)=O)CC#N)=NC=5)C=4)C=3)=CC=2)=CN=1)=O)C(C)C.COC(=O)NC(C(N1CCCC1C1NC(C2C=CC3C(=CC=C(C4C=CC(C5NC(C6CCCN6C(=O)C(NC(OC)=O)C(C)C)=NC=5)=CC=4)C=3)C=2)=CN=1)=O)C(C)C.COC(=O)NC(C(N1CCCC1C1NC(C2C=CC3C(=CC=C([B:233]4[O:237][C:236]([CH3:239])([CH3:238])[C:235]([CH3:241])([CH3:240])[O:234]4)C=3)C=2)=CN=1)=O)C(C)C>>[CH3:1][O:2][C:3](=[O:32])[NH:4][CH:5]([C:9]([N:11]1[CH:12]([C:16]2[NH:17][C:18]([C:23]3[CH:22]=[CH:21][C:54]4[C:53](=[CH:58][CH:57]=[C:56]([B:233]5[O:237][C:236]([CH3:239])([CH3:238])[C:235]([CH3:240])([CH3:241])[O:234]5)[CH:55]=4)[CH:49]=3)=[CH:19][N:88]=2)[CH:13]2[CH2:14][CH:15]1[CH2:78][CH2:79]2)=[O:10])[CH2:63][C:61]#[N:62]

Participants

Reactant 7

HCID 138211012-((Methoxycarbonyl)amino)-3-methylbutanoic acid

HCID 66620210[1-(2-{5-[6-(4-{2-[1-(2-Methoxycarbonylamino-3-methyl-butyryl)-pyrrolidin-2-yl]-3H-imidazol-4-yl}-phenyl)-naphthalen-2-yl}-1H-imidazol-2-yl]-pyrrolidine-1-carbonyl)-2-methyl-propyl]-carbamic acid methyl ester

HCID 666205302-(4'-Chloro-biphenyl-3-ylcarbamoyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

HCID 66620765[2-Methyl-1-(2-{4-[6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-naphthalen-2-yl]-1H-imidazol-2-yl}-pyrrolidine-1-carbonyl)-propyl]-carbamic acid methyl ester

HCID 66621127HCID 66621127, compound

HCID 66621197{1-[2-(4'-Chloro-biphenyl-3-ylcarbamoyl)-pyrrolidine-1-carbonyl]-2-methyl-propyl}-carbamic acid methyl ester

HCID 72338057HCID 72338057, compound

Product 1

HCID 66620428HCID 66620428, compound

Procedure

Title compound was prepared according to the method employed to prepare {1-[2-(4′-Chloro-biphenyl-3-ylcarbamoyl)-pyrrolidine-1-carbonyl]-2-methyl-propyl}-carbamic acid methyl ester (Example CX), substituting 3-{5-[6-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-naphthalen-2-yl]-1H-imidazol-2-yl}-2-aza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester for 2-(4′-Chloro-biphenyl-3-ylcarbamoyl)-pyrrolidine-1-carboxylic acid tert-butyl ester and 3-Cyano-2-methoxycarbonylamino-propionic acid for 2-methoxycarbonylamino-3-methyl-butyric acid. [1-(2-{5-[4-(6-{2-[2-(3-Cyano-2-methoxycarbonylamino-propionyl)-2-aza-bicyclo[2.2.1]hept-3-yl]-3H-imidazol-4-yl}-naphthalen-2-yl)-phenyl]-1H-imidazol-2-yl}-pyrrolidine-1-carbonyl)-2-methyl-propyl]-carbamic acid methyl ester: Title compound was prepared according to the method employed to prepare [1-(2-{5-[6-(4-{2-[1-(2-Methoxycarbonylamino-3-methyl-butyryl)-pyrrolidin-2-yl]-3H-imidazol-4-yl}-phenyl)-naphthalen-2-yl]-1H-imidazol-2-yl}-pyrrolidine-1-carbonyl)-2-methyl-propyl]-carbamic acid methyl ester (Example AZ), substituting [2-Cyano-1-(3-{5-[6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-naphthalen-2-yl]-1H-imidazol-2-yl}-2-aza-bicyclo[2.2.1]heptane-2-carbonyl)-ethyl]-carbamic acid methyl ester for [2-methyl-1-(2-{5-[6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-naphthalen-2-yl]-1H-imidazol-2-yl}-pyrrolidine-1-carbonyl)-propyl]-carbamic acid methyl ester. 1H NMR (DMSO-d6, 400 MHz) δ: 8.24-8.18 (m, 2H), 7.99-7.79 (m, 6H), 7.63-7.54 (m, 2H), 5.09 (m, 1H), 4.84 (m, 1H), 4.53 (s, 1H), 4.41 (s, 1H), 4.07 (m, 1H), 3.82 (m, 2H), 3.62 (s, 3H), 3.54 (s, 3H), 2.92-2.87 (m, 1H), 2.79-2.75 (m, 1H), 2.72-2.67 (m, 1H), 2.16-1.42 (m, 9H), 0.91-0.87 (m, 12H); MS (ESI) m/z 812 [M+H]+.

Workup

customTitle compound was prepared

Sources & evidence

ORD record: ord-a8f0763d81fe459bb20849792d988fe2
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08273341B2

Reaction notes

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