1-Chloroisoquinoline-7-carboxylic acid → 2'-tert-butyl-1-(1-chloroisoquinoline-7-carbonyl)-4',6'-dihydrospiro[piperidine-4,5'-pyrazolo[3,4-c]pyridin]-7'(2'H)-one

HRID 881012Notes

Reaction equation

HRID 881012 reaction equation
Cl.[C:2]([N:6]1[CH:14]=[C:13]2[C:8]([C:9](=[O:20])[NH:10][C:11]3([CH2:19][CH2:18][NH:17][CH2:16][CH2:15]3)[CH2:12]2)=[N:7]1)([CH3:5])([CH3:4])[CH3:3].[Cl:21][C:22]1[C:31]2[C:26](=[CH:27][CH:28]=[C:29]([C:32](O)=[O:33])[CH:30]=2)[CH:25]=[CH:24][N:23]=1>CN(C)C1C=CN=CC=1>[C:2]([N:6]1[CH:14]=[C:13]2[C:8]([C:9](=[O:20])[NH:10][C:11]3([CH2:19][CH2:18][N:17]([C:32]([C:29]4[CH:30]=[C:31]5[C:26]([CH:25]=[CH:24][N:23]=[C:22]5[Cl:21])=[CH:27][CH:28]=4)=[O:33])[CH2:16][CH2:15]3)[CH2:12]2)=[N:7]1)([CH3:5])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 211924911-Chloroisoquinoline-7-carboxylic acidHCID 674913562'-(tert-Butyl)-4',6'-dihydrospiro[piperidine-4,5'-pyrazolo[3,4-c]pyridin]-7'(2'H)-one hydrochloride2×

Product 1

HCID 866646192'-tert-butyl-1-(1-chloroisoquinoline-7-carbonyl)-4',6'-dihydrospiro[piperidine-4,5'-pyrazolo[3,4-c]pyridin]-7'(2'H)-one

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

The title compound was prepared by a method analogous to that described for Example 2, using 2′-tert-butyl-4′,6′-dihydrospiro[piperidine-4,5′-pyrazolo[3,4-c]pyridin]-7′(2′H)-one hydrochloride salt (Intermediate 4) and 1-chloroisoquinoline-7-carboxylic acid, and omitting 4-dimethylaminopyridine. +ESI (M+H) 452.3; 1H NMR (400 MHz, CDCl3, δ): 8.37 (s, 1H), 8.32 (d, J=5.7 Hz, 1H), 7.89 (d, J=8.4 Hz, 1H), 7.75-7.79 (m, 1H), 7.62 (d, J=5.7 Hz, 1H), 7.39 (s, 1H), 6.42 (s, 1H), 3.43-3.73 (m, 4H), 2.87 (s, 2H), 1.64-2.01 (m, 4H), 1.61 (s, 9H).

Sources & evidence

ORD record
ord-b6a84e631e404217afbc885592a2c002
Source dataset
uspto-grants-2015_03
Patent number
US08993586B2

Reaction notes

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