2(1H)-Isoquinolineacetic acid, 3,4-dihydro-, hydrochloride → HCID 67010812, compound

HRID 1630233Notes

Reaction equation

HRID 1630233 reaction equation
Cl.[CH2:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH2:4][N:3]1[CH2:12][C:13]([OH:15])=O.[CH2:16]([C@H:23]1[CH2:27][NH:26][C@H:25]([C:28]([NH:30][C:31]2[CH:36]=[CH:35][C:34]([O:37][C:38]3[CH:43]=[CH:42][C:41]([F:44])=[CH:40][CH:39]=3)=[CH:33][CH:32]=2)=[O:29])[CH2:24]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>>[CH2:16]([C@H:23]1[CH2:27][N:26]([C:13](=[O:15])[CH2:12][N:3]2[CH2:4][CH2:5][C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH2:2]2)[C@H:25]([C:28]([NH:30][C:31]2[CH:36]=[CH:35][C:34]([O:37][C:38]3[CH:39]=[CH:40][C:41]([F:44])=[CH:42][CH:43]=3)=[CH:33][CH:32]=2)=[O:29])[CH2:24]1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

3

Reactant 2

HCID 30757432(1H)-Isoquinolineacetic acid, 3,4-dihydro-, hydrochlorideHCID 67009148(2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide

Product 1

HCID 67010812HCID 67010812, compoundYield 34.7%

Procedure

Proceeding as in Example 1, but substituting 2-(3,4-dihydroisoquinolin-2(1H)-yl)acetic acid hydrochloride and (2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide, gave Compound 82, (2S,4R)-4-benzyl-1-(2-(3,4-dihydroisoquinolin-2(1H)-yl)acetyl)-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide (13.7 mg, 34.7%). Major isomer: 1H-NMR (400 MHz, DMSO-D6): σ 9.98 (s, 1H), 7.56 (d, 2H), 7.23-7.15 (m, 10H), 7.09 (m, 3H), 6.94 (m, 2H), 4.49 (m, 1H), 3.74 (m, 1H), 3.63 (d, 2H), 3.36 (m, 1H), 3.29 (s, 2H), 2.78-2.73 (m, 4H), 2.61 (m, 3H), 1.91 (m, 2H). MS (EI) for C35H34FN3O3. found 564.7 (MH+).

Sources & evidence

ORD record
ord-ccdd49d9eb094877ad5e598a48f9f756
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

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