HCID 67009398, compound → (S)-2-(2-(3,5-dimethyl-1H-pyrazol-4-yl)acetamido)-3-(4-fluorobenzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamide

HRID 1630172Notes

Reaction equation

HRID 1630172 reaction equation
Cl.[CH3:2][C:3]1[C:7]([CH2:8][C:9]([OH:11])=O)=[C:6]([CH3:12])[NH:5][N:4]=1.[NH2:13][C@@H:14]([CH2:32][O:33][CH2:34][C:35]1[CH:40]=[CH:39][C:38]([F:41])=[CH:37][CH:36]=1)[C:15]([NH:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=2)=[CH:20][CH:19]=1)=[O:16]>>[CH3:12][C:6]1[C:7]([CH2:8][C:9]([NH:13][C@@H:14]([CH2:32][O:33][CH2:34][C:35]2[CH:36]=[CH:37][C:38]([F:41])=[CH:39][CH:40]=2)[C:15]([NH:17][C:18]2[CH:19]=[CH:20][C:21]([O:24][C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=3)=[CH:22][CH:23]=2)=[O:16])=[O:11])=[C:3]([CH3:2])[NH:4][N:5]=1

Participants

3

Reactant 2

HCID 67009398HCID 67009398, compoundHCID 670104382-(3,5-dimethyl-1H-pyrazol-4-yl)acetic acid hydrochloride

Product 1

HCID 67009259(S)-2-(2-(3,5-dimethyl-1H-pyrazol-4-yl)acetamido)-3-(4-fluorobenzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamideYield 50%

Procedure

Proceeding as in Example 1, but substituting 2-(3,5-dimethyl-1H-pyrazol-4-yl)acetic acid hydrochloride and (S)-2-amino-3-(4-fluorobenzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamide, gave Compound 258, (S)-2-(2-(3,5-dimethyl-1H-pyrazol-4-yl)acetamido)-3-(4-fluorobenzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamide (70 mg, 50%). 1H-NMR (400 MHz, CDCl3): δ 8.55 (s, 1H), 7.40-7.25 (m, 6H), 7.15-6.90 (m, 7H), 6.50 (m, 1H), 4.79-4.73 (m, 1H), 4.63 (m, 2H), 3.80-3.50 (m, 4H), 2.20 (s, 6H). MS (EI) for C29H28F2N4O4 found 535 (MH+).

Sources & evidence

ORD record
ord-40cae25375e44f799cd0a9434baa673a
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

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