6-Aminoisoquinoline → HCID 49839840, compound

HRID 1889974Notes

Reaction equation

HRID 1889974 reaction equation
Cl[C:2]1[N:24]=[C:5]2[C:6]([NH:10][CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[N:18]([CH3:23])[S:19]([CH3:22])(=[O:21])=[O:20])=[CH:7][CH:8]=[CH:9][N:4]2[N:3]=1.[CH:25]1[C:34]2[C:29](=[CH:30][C:31]([NH2:35])=[CH:32][CH:33]=2)[CH:28]=[CH:27][N:26]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)CCCCC1>>[CH:25]1[C:34]2[C:29](=[CH:30][C:31]([NH:35][C:2]3[N:24]=[C:5]4[C:6]([NH:10][CH2:11][C:12]5[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=5[N:18]([CH3:23])[S:19]([CH3:22])(=[O:21])=[O:20])=[CH:7][CH:8]=[CH:9][N:4]4[N:3]=3)=[CH:32][CH:33]=2)[CH:28]=[CH:27][N:26]=1

Participants

4

Reactant 3

HCID 5889916-AminoisoquinolineHCID 249469872,2'-Bis(dicyclohexylphosphino)-1,1'-biphenylHCID 67479080N-{2-[(2-Chloro-[1,2,4]triazolo[1,5-a]pyridin-8-ylamino)-methyl]-phenyl}-N-methyl-methanesulfonamide

Product 1

HCID 49839840HCID 49839840, compound

Procedure

N-(2-{[2-(Isoquinolin-6-ylamino)-[1,2,4]triazolo[1,5-a]pyridin-8-ylamino]-methyl}-phenyl)-N-methyl-methanesulfonamide was prepared from N-{2-[(2-chloro-[1,2,4]triazolo[1,5-a]pyridin-8-ylamino)-methyl]-phenyl}-N-methyl-methanesulfonamide (100.0 mg, 0.2733 mmol) and isoquinolin-6-ylamine (45.0 mg, 0.312 mmol) with 2,2′-bis-dicyclohexylphosphanyl-biphenyl (25.0 mg, 0.0457 mmol) as the ligand in a manner analogous to Example 2d. Product isolated as a yellow foam (0.079 g, 61%). 1H NMR (400 MHz, CDCl3, δ, ppm): 9.09 (s, 1H), 8.43 (d, J=5.1 Hz, 1H), 8.28 (s, 1H), 7.92-7.87 (m, 2H), 7.62 (d, J=5.3 Hz, 1H), 7.54 (d, J=6.8 Hz, 2H), 7.40-7.28 (m, 3H), 7.18 (s, 1H), 6.76 (t, J=7.0 Hz, 1H), 6.44 (d, J=7.3 Hz, 1H), 5.39-5.32 (m, 1H), 4.75 (d, J=5.4 Hz, 2H), 3.32 (s, 3H), 3.02 (s, 3H). MS=474 (MH)+.

Sources & evidence

ORD record
ord-4ad4587e3ebf4ab7a1240fce3af69e6d
Source dataset
uspto-grants-2013_08
Patent number
US08501936B2

Reaction notes

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