HCID 67009785, compound → HCID 178520355, compound

HRID 1630153Notes

Reaction equation

HRID 1630153 reaction equation
Cl.[NH:2]1[CH:6]=[C:5]([CH2:7][C:8]([OH:10])=O)[N:4]=[CH:3]1.[NH2:11][C@@H:12]([CH2:29][O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:13]([NH:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([O:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:17]=1)=[O:14]>>[NH:2]1[CH:6]=[C:5]([CH2:7][C:8]([NH:11][C@@H:12]([CH2:29][O:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:13]([NH:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([O:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH:17]=2)=[O:14])=[O:10])[N:4]=[CH:3]1

Participants

3

Reactant 2

HCID 67009785HCID 67009785, compoundHCID 178479752HCID 178479752, compound

Product 1

HCID 178520355HCID 178520355, compoundYield 21%

Procedure

Proceeding as in Example 1, but substituting 1H-imidazol-4-ylacetic acid hydrochloride and (S)-2-amino-3-(benzyloxy)-N-(3-phenoxyphenyl)propanamide, gave Compound 243, (S)-2-(2-(1H-imidazol-4-yl)acetamido)-3-(benzyloxy)-N-(3-phenoxyphenyl)propanamide (100 mg, 21%); Major isomer: 1H-NMR (400 MHz, DMSO-D6): σ 11.87 (br s, 1H), 10.28 (s, 1H), 8.42-8.41 (d, 1H), 7.54-7.43 (m, 10H), 7.18-7.14 (t, 1H), 7.05-7.03 (d, 2H), 6.95 (s, 1H), 6.75-6.67 (d, 1H), 4.69-4.62 (m, 1H), 4.49 (s, 1H), 3.69-3.60 (m, 2H), 3.51-3.40 (m, 2H). MS (EI) for C27H26N4O4. found 471.0 (MH+).

Sources & evidence

ORD record
ord-6023ae71a7b74616b9d8cfcb32d0502a
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

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