5-(3-(9-(4-methoxybenzyl)-9H-purin-6-yl)pyridin-2-yloxy)-N-(4-chlorophenyl)-6-methylisoquinolin-1-amine → HCID 178422909, compound

HRID 1042283Notes

Reaction equation

HRID 1042283 reaction equation
COC1C=CC(C[N:8]2[CH:16]=[N:15][C:14]3[C:9]2=[N:10][CH:11]=[N:12][C:13]=3[C:17]2[C:18]([O:23][C:24]3[C:33]([CH3:34])=[CH:32][CH:31]=[C:30]4[C:25]=3[CH:26]=[CH:27][N:28]=[C:29]4[NH:35][C:36]3[CH:41]=[CH:40][C:39]([Cl:42])=[CH:38][CH:37]=3)=[N:19][CH:20]=[CH:21][CH:22]=2)=CC=1>C(O)(C(F)(F)F)=O>[N:12]1[C:13]([C:17]2[C:18]([O:23][C:24]3[C:33]([CH3:34])=[CH:32][CH:31]=[C:30]4[C:25]=3[CH:26]=[CH:27][N:28]=[C:29]4[NH:35][C:36]3[CH:41]=[CH:40][C:39]([Cl:42])=[CH:38][CH:37]=3)=[N:19][CH:20]=[CH:21][CH:22]=2)=[C:14]2[C:9]([NH:8][CH:16]=[N:15]2)=[N:10][CH:11]=1

Participants

3

Reactant 1

HCID 687422985-(3-(9-(4-methoxybenzyl)-9H-purin-6-yl)pyridin-2-yloxy)-N-(4-chlorophenyl)-6-methylisoquinolin-1-amine

Product 1

HCID 178422909HCID 178422909, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 5-(3-(9-(4-methoxybenzyl)-9H-purin-6-yl)pyridin-2-yloxy)-N-(4-chlorophenyl)-6-methylisoquinolin-1-amine (0.22 g, 0.37 mmol) in TFA (5 mL) was stirred in a 65° C. oil bath for 3.5 h. The TFA was removed in vacuo and the residue was dissolved in MeOH (50 mL) and 2 M NH3 in MeOH (50 mL) and adsorbed onto a pad of silica gel. The crude product was chromatographed through a Redi-Sep® pre-packed silica gel column (12 g), eluting with a gradient of 1% to 8% 1 M NH3.MeOH in CH2Cl2 (over 20 min), to give 5-(3-(9H-purin-6-yl)pyridin-2-yloxy)-N-(4-chlorophenyl)-6-methylisoquinolin-1-amine as a white solid. 1H NMR (400 MHz, DMSO-d6) □ ppm 2.23 (s, 3H), 7.24-7.33 (m, 2H), 7.35 (d, J=8.53 Hz, 2H), 7.53 (d, J=8.53 Hz, 1H), 7.88-7.97 (m, 3H), 8.13 (d, J=5.02 Hz, 1H), 8.24 (d, J=7.53 Hz, 1H), 8.34 (d, J=8.53 Hz, 1H), 8.68 (s, 1H), 9.07 (s, 1H), 9.27 (s, 1H), 13.64 (s, 1H); MS (ESI, pos. ion) m/z: 480.1 [M+H]+

Workup

  1. customThe TFA was removed in vacuo
  2. dissolutionthe residue was dissolved in MeOH (50 mL)
  3. customThe crude product was chromatographed through a Redi-Sep® pre-packed silica gel column (12 g)
  4. washeluting with a gradient of 1% to 8% 1 M NH3

Sources & evidence

ORD record
ord-f7541f5e6023463b89077afe3f7aa260
Source dataset
uspto-grants-2013_10
Patent number
US08557830B2

Reaction notes

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