HCID 46735248, compound → HCID 67009740, compound

HRID 1630102Notes

Reaction equation

HRID 1630102 reaction equation
Cl.[N:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[CH2:8][C:9]([OH:11])=O.[NH2:12][C@@H:13]([CH2:31][O:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[C:14]([NH:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=2)=[CH:19][CH:18]=1)=[O:15]>>[CH2:33]([O:32][CH2:31][C@H:13]([NH:12][C:9](=[O:11])[CH2:8][C:3]1[CH:4]=[N:5][CH:6]=[CH:7][N:2]=1)[C:14]([NH:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=2)=[CH:19][CH:18]=1)=[O:15])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

3

Reactant 2

HCID 46735248HCID 46735248, compoundHCID 67009137(S)-2-amino-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamide

Product 1

HCID 67009740HCID 67009740, compoundYield 46%

Procedure

Proceeding as in Example 1, but substituting 2-(pyrazin-2-yl)acetic acid hydrochloride and (S)-2-amino-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamide, gave Compound 159, (S)-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)-2-(2-(pyrazin-2-yl)acetamido)propanamide (66 mg, 46%). 1H-NMR (400 MHz, CDCl3): σ 8.63-8.44 (m, 4H), 7.40-7.19 (m, 9H), 7.05-6.92 (m, 3H), 4.74-4.70 (m, 1H), 4.66 (d, 1H), 4.55 (d, 1H), 4.10 (dd, 1H), 3.85 (s, 2H), 3.64 (dd, 1H). MS (EI) for C28H25FN4O4. found 501.2 (MH+).

Sources & evidence

ORD record
ord-bbe7d74d872a4364b67952b21d39fc59
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

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