1-Cyclopropyl-5-(2-hydroxyethoxy)isoquinoline-7-carboxylic acid → n-(2-Amino-2-oxoethyl)-1'-{[1-cyclopropyl-5-(2-hydroxyethoxy)isoquinolin-7-yl]carbonyl}-4-oxospiro[chroman-2,4'-piperidine]-6-carboxamide

HRID 545187Notes

Reaction equation

HRID 545187 reaction equation
Cl.[C:2]([CH2:5][NH:6][C:7]([C:9]1[CH:10]=[C:11]2[C:21](=[CH:22][CH:23]=1)[O:20][C:14]1([CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1)[CH2:13][C:12]2=[O:24])=[O:8])(=[O:4])[NH2:3].[CH:25]1([C:28]2[C:37]3[C:32](=[C:33]([O:41][CH2:42][CH2:43][OH:44])[CH:34]=[C:35]([C:38](O)=[O:39])[CH:36]=3)[CH:31]=[CH:30][N:29]=2)[CH2:27][CH2:26]1.C1(C2C3C(=C(OC)C=C(C(O)=O)C=3)C=CN=2)CC1>>[NH2:3][C:2](=[O:4])[CH2:5][NH:6][C:7]([C:9]1[CH:10]=[C:11]2[C:21](=[CH:22][CH:23]=1)[O:20][C:14]1([CH2:19][CH2:18][N:17]([C:38]([C:35]3[CH:36]=[C:37]4[C:32]([CH:31]=[CH:30][N:29]=[C:28]4[CH:25]4[CH2:26][CH2:27]4)=[C:33]([O:41][CH2:42][CH2:43][OH:44])[CH:34]=3)=[O:39])[CH2:16][CH2:15]1)[CH2:13][C:12]2=[O:24])=[O:8]

Participants

4

Reactant 3

HCID 574408911-Cyclopropyl-5-(2-hydroxyethoxy)isoquinoline-7-carboxylic acidHCID 574408921-Cyclopropyl-5-methoxyisoquinoline-7-carboxylic acidHCID 66649519N-Carbamoylmethyl-4-oxospiro[chroman-2,4'-piperidine]-6-carboxamide hydrochloride

Product 1

HCID 16042868n-(2-Amino-2-oxoethyl)-1'-{[1-cyclopropyl-5-(2-hydroxyethoxy)isoquinolin-7-yl]carbonyl}-4-oxospiro[chroman-2,4'-piperidine]-6-carboxamide

Procedure

The intended compound was produced according to the procedure described in reference Example 37 but using 4-oxospiro(chroman-2,4′-piperidin)-6-yl-carboxylicacidcarbamoylmethyl amide hydrochloride and 1-cyclopropyl-5-(2-hydroxy-ethoxy)-isoquinoline-7-carboxylic acid in place of methyl 5″-{4-oxospiro[chroman-2,4′-piperidin]-6-yl}nicotinate di-hydrochloride and 1-cyclopropyl-5-methoxy-isoquinoline-7-carboxylic acid. 1H-NMR (400 MHz, DMSO-d6) δ: 8.75 (1.0H, t, J=5.7 Hz), 8.36 (1.0H, d, J=5.7 Hz), 8.31 (1.0H, d, J=2.4 Hz), 8.09 (1.0H, dd, J=8.8, 2.4 Hz), 8.05 (1.0H, s), 7.85 (1.0H, d, J=5.9 Hz), 7.34 (1.0H, s), 7.22-7.14 (2.0H, m), 6.99 (1.0H, s), 5.00 (1.0H, t, J=5.7 Hz), 4.39-4.25 (1.0H, m), 4.21 (2.0H, t, J=4.8 Hz), 3.84 (2.0H, q, J=4.8 Hz), 3.78 (2.0H, d, J=5.9 Hz), 3.62-3.17 (3.0H, m), 2.95 (2.0H, s), 2.93-2.85 (1.0H, m), 2.15-1.77 (4.0H, m), 1.15-0.99 (4.0H, m). MS [M]+572.

Workup

  1. customThe intended compound was produced

Sources & evidence

ORD record
ord-76202b511d6640619a06a8cf4d8e97cc
Source dataset
uspto-grants-2011_05
Patent number
US07935712B2

Reaction notes

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