6-Aminoisoquinoline → HCID 59513799, compound

HRID 1159898Notes

Reaction equation

HRID 1159898 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]2[C:9]([C:17]3[CH:18]=[C:19]([NH:23][C:24](=[O:33])[C:25]4[C:30]([F:31])=[CH:29][CH:28]=[CH:27][C:26]=4[F:32])[CH:20]=[CH:21][CH:22]=3)=[N:10][N:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=23)[CH:5]=[CH:4][N:3]=1.[CH:34]1[C:43]2[C:38](=[CH:39][C:40]([NH2:44])=[CH:41][CH:42]=2)[CH:37]=[CH:36][N:35]=1>CC(O)C>[F:32][C:26]1[CH:27]=[CH:28][CH:29]=[C:30]([F:31])[C:25]=1[C:24]([NH:23][C:19]1[CH:20]=[CH:21][CH:22]=[C:17]([C:9]2[C:8]([C:6]3[CH:5]=[CH:4][N:3]=[C:2]([NH:44][C:40]4[CH:39]=[C:38]5[C:43](=[CH:42][CH:41]=4)[CH:34]=[N:35][CH:36]=[CH:37]5)[N:7]=3)=[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][N:11]3[N:10]=2)[CH:18]=1)=[O:33]

Participants

4

Reactant 2

HCID 5889916-Aminoisoquinoline2×HCID 59513803N-{3-[3-(2-Chloro-4-pyrimidinyl)pyrazolo[1,5-a]pyridin-2-yl]phenyl}-2,6-difluorobenzamide

Product 1

HCID 59513799HCID 59513799, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of N-{3-[3-(2-chloro-4-pyrimidinyl)pyrazolo[1,5-a]pyridin-2-yl]phenyl}-2,6-difluorobenzamide and 6-isoquinolinamine and 6-isoquinolinamine in i-PrOH was heated in a microwave in a procedure analogous to that described in Example 64 to give, after purification, the title compound. LC MS (ES)+ 570.25. 1H NMR (400 MHz, DMSO-d6) δ 6.95 (s, 1H), 7.17-7.30 (m, 4H), 7.41 (d, 1H, J=7.5), 7.51-7.56 (m, 3H), 7.64 7.68 (m, 1H), 7.78-7.81 (m, 2H), 8.05 (s, 1H), 8.09 (bs, 2H), 8.19 (d, 1H, J=9.1), 8.41 (d, 1H, J=9.0), 8.85-8.89 (m, 2H), 8.96 (d, 1H, J=6.8), 9.8 (s, 1H), 10.94 (s, 1H).

Workup

  1. temperaturewas heated in a microwave in a procedure analogous to
  2. customto give
  3. customafter purification

Sources & evidence

ORD record
ord-911be389d4fb45d999106008dd1d5952
Source dataset
uspto-grants-2010_10
Patent number
US07812022B2

Reaction notes

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