2-[5-(4-bromo-phenyl)-1H-imidazol-2-yl]-pyrrolidine-1-carboxylic acid tert-butyl ester → HCID 69672730, compound

HRID 1751441Notes

Reaction equation

[C:1](OC(N1CCCC1C1NC(C2C=CC(C3C=CC4C(=CC=C(C5NC(C6CCCN6C(=O)C(NC(OC)=O)C(C)C)=NC=5)C=4)C=3)=CC=2)=CN=1)=O)(C)(C)[CH3:2].[C:55]([O:59][C:60]([N:62]1[CH2:66][CH2:65][CH2:64][CH:63]1[C:67]1[NH:68][C:69]([C:72]2[CH:77]=[CH:76][C:75](Br)=[CH:74][CH:73]=2)=[CH:70][N:71]=1)=[O:61])([CH3:58])([CH3:57])[CH3:56].C(OC(N1CCCC1C1NC(C2C=CC3C(=CC=C(B4OC(C)(C)C(C)(C)O4)C=3)C=2)=CN=1)=O)(C)(C)C.[CH3:115][O:116][C:117](=[O:154])[NH:118][CH:119]([C:123]([N:125]1[CH2:129][CH2:128][CH2:127][CH:126]1[C:130]1[NH:131][C:132]([C:135]2[CH:144]=[CH:143][C:142]3[C:137](=CC=[C:140](B4OC(C)(C)C(C)(C)O4)[CH:141]=3)[CH:136]=2)=[CH:133][N:134]=1)=[O:124])[CH:120]([CH3:122])[CH3:121]>>[C:55]([O:59][C:60]([N:62]1[CH2:66][CH2:65][CH2:64][CH:63]1[C:67]1[NH:68][C:69]([C:72]2[CH:77]=[CH:76][C:75]3[C:74](=[CH:1][CH:2]=[C:141]([C:142]4[CH:143]=[CH:144][C:135]([C:132]5[NH:131][C:130]([CH:126]6[CH2:127][CH2:128][CH2:129][N:125]6[C:123](=[O:124])[CH:119]([NH:118][C:117]([O:116][CH3:115])=[O:154])[CH:120]([CH3:122])[CH3:121])=[N:134][CH:133]=5)=[CH:136][CH:137]=4)[CH:140]=3)[CH:73]=2)=[CH:70][N:71]=1)=[O:61])([CH3:58])([CH3:57])[CH3:56]

Participants

Reactant 4

HCID 547756232-[5-(4-bromo-phenyl)-1H-imidazol-2-yl]-pyrrolidine-1-carboxylic acid tert-butyl ester

HCID 666204642-{5-[4-(6-{2-[1-(2-Methoxycarbonylamino-3-methyl-butyryl)-pyrrolidin-2-yl]-3H-imidazol-4-yl]-naphthalen-2-yl)-phenyl]-1H-imidazol-2-yl]-pyrrolidine-1-carboxylic acid tert-butyl ester

HCID 666205222-{5-[6-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-naphthalen-2-yl]-1H-imidazol-2-yl]-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

Product 1

HCID 69672730HCID 69672730, compound

Procedure

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-carboxylic acid tert-butyl ester was prepared following the procedure for 2-{5-[4-(6-{2-[1-(2-Methoxycarbonylamino-3-methyl-butyryl)-pyrrolidin-2-yl]-3H-imidazol-4-yl}-naphthalen-2-yl)-phenyl]-1H-imidazol-2-yl}-pyrrolidine-1-carboxylic acid tert-butyl ester, substituting (1-{2-[5-(4-Bromo-phenyl)-1H-imidazol-2-yl]-pyrrolidine-1-carbonyl}-2-methyl-propyl)-carbamic acid methyl ester for 2-[5-(4-Bromo-phenyl)-1H-imidazol-2-yl]-pyrrolidine-1-carboxylic acid tert-butyl ester and 2-{5-[6-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-naphthalen-2-yl]-1H-imidazol-2-yl}-pyrrolidine-1-carboxylic acid tert-butyl 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. LCMS-ESI+: calc'd for C42H49N7O5: 731.4 (M+); Found: 732.9 (M+H+).

Sources & evidence

ORD record: ord-289cd66ab8cc4681b5f1feb144fa0e99
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09156823B2

Reaction notes

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