Diisopropylethylamine → HCID 178502147, compound

HRID 1751525Notes

Reaction equation

HRID 1751525 reaction equation
[CH3:1][O:2][C:3](=[O:59])[NH:4][CH:5]([C:9]([N:11]1[CH2:15][CH2:14][CH2:13][CH:12]1[C:16]1[NH:20][C:19]2[C:21]3[C:26]([CH:27]=[CH:28][C:18]=2[N:17]=1)=[CH:25][C:24]([C:29]1[CH:38]=[CH:37][C:36]2[C:31](=[CH:32][CH:33]=[C:34]([C:39]4[NH:40][C:41]([CH:44]5[CH2:48][CH2:47][CH2:46][N:45]5[C:49](=[O:58])[CH:50]([NH2:57])[C:51]5[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=5)=[N:42][CH:43]=4)[CH:35]=2)[CH:30]=1)=[CH:23][CH:22]=3)=[O:10])[CH:6]([CH3:8])[CH3:7].CCN(C(C)C)C(C)C.[O:69]1[CH2:72][CH:71]([O:73][C:74](=O)[O:75]C2C=CC([N+]([O-])=O)=CC=2)[CH2:70]1>C(#N)C>[CH3:1][O:2][C:3](=[O:59])[NH:4][CH:5]([C:9]([N:11]1[CH2:15][CH2:14][CH2:13][CH:12]1[C:16]1[NH:20][C:19]2[C:21]3[C:26]([CH:27]=[CH:28][C:18]=2[N:17]=1)=[CH:25][C:24]([C:29]1[CH:38]=[CH:37][C:36]2[C:31](=[CH:32][CH:33]=[C:34]([C:39]4[NH:40][C:41]([CH:44]5[CH2:48][CH2:47][CH2:46][N:45]5[C:49](=[O:58])[CH:50]([NH:57][C:74]([O:73][CH:71]5[CH2:72][O:69][CH2:70]5)=[O:75])[C:51]5[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=5)=[N:42][CH:43]=4)[CH:35]=2)[CH:30]=1)=[CH:23][CH:22]=3)=[O:10])[CH:6]([CH3:8])[CH3:7]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 66905273HCID 66905273, compoundHCID 178502146HCID 178502146, compound

Product 1

HCID 178502147HCID 178502147, compoundYield 311.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

(1-{2-[7-(6-{2-[1-(2-Amino-2-phenyl-acetyl)-pyrrolidin-2-yl]-3H-imidazol-4-yl}-naphthalen-2-yl)-1H-naphtho[1,2-d]imidazol-2-yl]-pyrrolidine-1-carbonyl}-2-methyl-propyl)-carbamic acid methyl ester (0.200 g, 0.22 mmol) was dissolved in acetonitrile (2.2 mL). DIPEA (0.155 mL, 0.8905 mmol) and Carbonic acid 4-nitro-phenyl ester oxetan-3-yl ester (0.059 g, 0.244 mmol) was added, and the solution was allowed to stir for about three hours. Upon completion, the crude product was purified by reverse phase HPLC (10-50% acetonitrile:water; 0.1% formic acid modifier), and lyophilized giving [2-Methyl-1-(2-{7-[6-(2-{1-[2-(oxetan-3-yloxycarbonylamino)-2-phenyl-acetyl]-pyrrolidin-2-yl}-3H-imidazol-4-yl)-naphthalen-2-yl]-1H-naphtho[1,2-d]imidazol-2-yl}-pyrrolidine-1-carbonyl)-propyl]-carbamic acid methyl ester (0.61 g, 31% yield). LCMS-ESI+: calc'd for C51H52N8O7: 888.40 (M+); Found: 889.86 (M+H+).

Workup

  1. customUpon completion, the crude product was purified by reverse phase HPLC (10-50% acetonitrile:water; 0.1% formic acid modifier)

Sources & evidence

ORD record
ord-7518489dee144d50996f463beb1a56b1
Source dataset
uspto-grants-2015_10
Patent number
US09156823B2

Reaction notes

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