(1H-1,2,3-Triazol-1-yl)acetic acid--hydrogen chloride (1/1) → HCID 67010698, compound

HRID 1630171Notes

Reaction equation

HRID 1630171 reaction equation
Cl.[N:2]1([CH2:7][C:8]([OH:10])=O)[CH:6]=[CH:5][N:4]=[N:3]1.[NH2:11][C@@H:12]([CH2:30][O:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[C:13]([NH:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=2)=[CH:18][CH:17]=1)=[O:14]>>[N:2]1([CH2:7][C:8]([NH:11][C@@H:12]([CH2:30][O:31][CH2:32][C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)[C:13]([NH:15][C:16]2[CH:17]=[CH:18][C:19]([O:22][C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=3)=[CH:20][CH:21]=2)=[O:14])=[O:10])[CH:6]=[CH:5][N:4]=[N:3]1

Participants

3

Reactant 2

HCID 45357676(1H-1,2,3-Triazol-1-yl)acetic acid--hydrogen chloride (1/1)HCID 67009137(S)-2-amino-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamide

Product 1

HCID 67010698HCID 67010698, compoundYield 7%

Procedure

Proceeding as in Example 1, but substituting 2-(1H-1,2,3-triazol-1-yl)acetic acid hydrochloride and (S)-2-amino-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamide, gave Compound 174, (S)-2-(2-(1H-1,2,3-triazol-1-yl)acetamido)-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamide (17.6 mg, 7%). 1H-NMR (400 MHz, CDCl3): σ 8.37 (s, 1H), 7.80 (s, 1H), 7.74 (s, 1H), 7.38-7.29 (m, 6H), 7.02 (t, 2H), 6.96-6.91 (m, 4H), 6.85 (d, 1H), 5.19-5.11 (m, 2H), 4.70-4.65 (m, 1H), 4.64 (d, 1H), 4.55 (d, 1H), 3.98 (dd, 1H), 3.58 (t, 1H). MS (EI) for C26H24FN5O4. found 490.2 (MH+).

Sources & evidence

ORD record
ord-4024c5ee6320470486de640374d89c3b
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

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