2-(1H-1,2,4-triazol-1-yl)acetic acid hydrochloride → (S)-benzyl 4-(2-(1H-1,2,4-triazol-1-yl)acetamido)-5-(4-(4-fluorophenoxy)phenylamino)-5-oxopentylcarbamate

HRID 1630091Notes

Reaction equation

HRID 1630091 reaction equation
[NH2:1][C@H:2]([C:17]([NH:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][C:27]2[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=2)=[CH:22][CH:21]=1)=[O:18])[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[O:16])[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.Cl.[N:35]1([CH2:40][C:41](O)=[O:42])[CH:39]=[N:38][CH:37]=[N:36]1>>[N:35]1([CH2:40][C:41]([NH:1][C@H:2]([C:17]([NH:19][C:20]2[CH:21]=[CH:22][C:23]([O:26][C:27]3[CH:28]=[CH:29][C:30]([F:33])=[CH:31][CH:32]=3)=[CH:24][CH:25]=2)=[O:18])[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[O:16])[O:8][CH2:9][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)=[O:42])[CH:39]=[N:38][CH:37]=[N:36]1

Participants

3

Reactant 2

HCID 448870502-(1H-1,2,4-triazol-1-yl)acetic acid hydrochlorideHCID 86659466(S)-benzyl 4-amino-5-(4-(4-fluorophenoxy)phenylamino)-5-oxopentylcarbamate

Product 1

HCID 70641275(S)-benzyl 4-(2-(1H-1,2,4-triazol-1-yl)acetamido)-5-(4-(4-fluorophenoxy)phenylamino)-5-oxopentylcarbamateYield 20%

Procedure

Proceeding as in Example 1, but substituting (S)-benzyl 4-amino-5-(4-(4-fluorophenoxy)phenylamino)-5-oxopentylcarbamate and 2-(1H-1,2,4-triazol-1-yl)acetic acid hydrochloride, gave Compound 165, (S)-benzyl 4-(2-(1H-1,2,4-triazol-1-yl)acetamido)-5-(4-(4-fluorophenoxy)phenylamino)-5-oxopentylcarbamate (90.1 mg, 20%). 1H-NMR (400 MHz, DMSO-D6): σ 10.19 (s, 1H), 8.69 (d, 1H), 8.48 (s, 1H), 7.96 (s, 1H), 7.60 (d, 2H), 7.39-7.29 (m, 5H), 7.21 (m, 2H), 7.04-6.96 (m, 4H), 5.00-4.97 (m, 4H), 4.46-4.39 (m, 1H), 3.04-2.99 (m, 2H), 1.75-1.39 (m, 4H). MS (EI) for C29H29FN6O5. found 560.9 (MH+).

Sources & evidence

ORD record
ord-ec9d56f1a42b434280ee8893a19917ea
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

Loading…