2(1H)-Isoquinolineacetic acid, 3,4-dihydro-, hydrochloride → HCID 67010117, compound

HRID 1630119Notes

Reaction equation

HRID 1630119 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.[NH2:16][C@@H:17]([CH2:35][O:36][CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[C:18]([NH:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][C:28]2[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=2)=[CH:23][CH:22]=1)=[O:19]>>[CH2:37]([O:36][CH2:35][C@H:17]([NH:16][C:13](=[O:15])[CH2:12][N:3]1[CH2:4][CH2:5][C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH2:2]1)[C:18]([NH:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][C:28]2[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=2)=[CH:23][CH:22]=1)=[O:19])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1

Participants

3

Reactant 2

HCID 30757432(1H)-Isoquinolineacetic acid, 3,4-dihydro-, hydrochlorideHCID 67009137(S)-2-amino-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamide

Product 1

HCID 67010117HCID 67010117, compoundYield 35.2%

Procedure

Proceeding as in Example 1, but substituting 2-(3,4-dihydroisoquinolin-2(1H)-yl)acetic acid hydrochloride and (S)-2-amino-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamide, gave Compound 221, (S)-3-(benzyloxy)-2-(2-(3,4-dihydroisoquinolin-2(1H)-yl)acetamido)-N-(4-(4-fluorophenoxy)phenyl)propanamide (15.6 mg, 35.2%); Major isomer: 1H-NMR (400 MHz, DMSO-D6): σ 10.20 (s, 1H), 8.03 (d, 1H), 7.60 (d, 2H), 7.22-7.26 (m, 5H), 7.19-7.21 (m, 2H), 7.12-7.15 (m, 3H), 6.98-7.04 (m, 5H), 4.73 (m, 1H), 4.50 (s, 2H), 3.71-3.79 (m, 2H), 3.70 (s, 2H), 3.18 (s, 2H), 2.83-2.86 (m, 2H), 2.71-2.81 (m, 2H). MS (EI) for C33H32FN3O4: 554.6 (MH+).

Sources & evidence

ORD record
ord-43f858dd7013466295c6ddb12ef5cf13
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

Loading…