4-N,N-dimethylaminophenylacetic acid → HCID 67009557, compound

HRID 1630225Notes

Reaction equation

HRID 1630225 reaction equation
[CH3:1][N:2]([CH3:13])[C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([OH:12])=O)=[CH:5][CH:4]=1.[CH2:14]([C@H:21]1[CH2:25][NH:24][C@H:23]([C:26]([NH:28][C:29]2[CH:34]=[CH:33][C:32]([O:35][C:36]3[CH:41]=[CH:40][C:39]([F:42])=[CH:38][CH:37]=3)=[CH:31][CH:30]=2)=[O:27])[CH2:22]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>>[CH2:14]([C@H:21]1[CH2:25][N:24]([C:10](=[O:12])[CH2:9][C:6]2[CH:5]=[CH:4][C:3]([N:2]([CH3:1])[CH3:13])=[CH:8][CH:7]=2)[C@H:23]([C:26]([NH:28][C:29]2[CH:34]=[CH:33][C:32]([O:35][C:36]3[CH:37]=[CH:38][C:39]([F:42])=[CH:40][CH:41]=3)=[CH:31][CH:30]=2)=[O:27])[CH2:22]1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

3

Reactant 2

HCID 1522034-N,N-dimethylaminophenylacetic acidHCID 67009148(2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide

Product 1

HCID 67009557HCID 67009557, compoundYield 7.6%

Procedure

Proceeding as in Example 1, but substituting 2-(4-(dimethylamino)phenyl)acetic acid and (2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide, gave Compound 35, (2S,4R)-4-benzyl-1-(2-(4-(dimethylamino)phenyl)acetyl)-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide (2.5 mg, 7.6%). 1H-NMR (400 MHz, DMSO-D6): σ 9.95 (s, 1H), 7.56 (m, 2H), 7.23 (t, 2H), 7.12 (m, 5H), 6.98 (m, 6H), 6.64 (m, 2H), 4.46 (m, 1H), 3.49 (s, 2H), 3.24 (m, 1H), 2.84 (s, 6H), 2.60 (m, 3H), 1.87 (m, 2H). MS (EI) for C34H34FN3O3: 552.6 (MH+).

Sources & evidence

ORD record
ord-10a0dd16ef57485daa99905bfa145063
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

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