(2,6-Dimethylmorpholin-4-yl)acetic acid--hydrogen chloride (1/1) → HCID 67009462, compound

HRID 1630113Notes

Reaction equation

HRID 1630113 reaction equation
Cl.[CH3:2][CH:3]1[CH2:8][N:7]([CH2:9][C:10]([OH:12])=O)[CH2:6][CH:5]([CH3:13])[O:4]1.[NH2:14][C@@H:15]([CH2:33][O:34][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[C:16]([NH:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][C:26]2[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=2)=[CH:21][CH:20]=1)=[O:17]>>[CH2:35]([O:34][CH2:33][C@H:15]([NH:14][C:10](=[O:12])[CH2:9][N:7]1[CH2:6][CH:5]([CH3:13])[O:4][CH:3]([CH3:2])[CH2:8]1)[C:16]([NH:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][C:26]2[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=2)=[CH:21][CH:20]=1)=[O:17])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Participants

3

Reactant 2

HCID 44118486(2,6-Dimethylmorpholin-4-yl)acetic acid--hydrogen chloride (1/1)HCID 67009137(S)-2-amino-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamide

Product 1

HCID 67009462HCID 67009462, compoundYield 25.9%

Procedure

Proceeding as in Example 1, but substituting 2-(2,6-dimethylmorpholino)acetic acid hydrochloride and (S)-2-amino-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamide, gave Compound 265, (2S)-3-(benzyloxy)-2-(2-(2,6-dimethylmorpholino)acetamido)-N-(4-(4-fluorophenoxy)phenyl)propanamide (11.1 mg, 25.9%); Major isomer: 1H-NMR (400 MHz, DMSO-D6): σ 10.20 (s, 1H), 7.98 (d, 1H), 7.60 (d, 2H), 7.27-7.32 (m, 5H), 7.19-7.23 (m, 2H), 6.98-7.04 (m, 4H), 4.69-4.71 (m, 1H), 4.52 (s, 2H), 3.71-3.77 (m, 2H), 3.54-3.5 (m, 2H), 2.93-3.03 (m, 2H), 2.74 (dd, 2H), 1.73-1.80 (m, 2H), 1.00 (dd, 6H). MS (EI) for C30H34FN3O5. found 536.6 (MH+).

Sources & evidence

ORD record
ord-74dd4edb7c304a13b9e2fa2ef13eaf58
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

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