4,4-Dimethyl-7-{2-[(2-methylamino-pyrimidin-4-ylmethyl)-amino]-benzoylamino}-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester → N-(4,4-Dimethyl-1,2,3,4-tetrahydro-isoquinolin-7-yl)-2-[(2-methylamino-pyrimidin-4-ylmethyl)-amino]-benzamide

HRID 969697Notes

Reaction equation

HRID 969697 reaction equation
C(OC([N:8]1[CH2:17][C:16]([CH3:19])([CH3:18])[C:15]2[C:10](=[CH:11][C:12]([NH:20][C:21](=[O:38])[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[NH:28][CH2:29][C:30]3[CH:35]=[CH:34][N:33]=[C:32]([NH:36][CH3:37])[N:31]=3)=[CH:13][CH:14]=2)[CH2:9]1)=O)(C)(C)C>C(O)(C(F)(F)F)=O.C(Cl)Cl>[CH3:18][C:16]1([CH3:19])[C:15]2[C:10](=[CH:11][C:12]([NH:20][C:21](=[O:38])[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[NH:28][CH2:29][C:30]3[CH:35]=[CH:34][N:33]=[C:32]([NH:36][CH3:37])[N:31]=3)=[CH:13][CH:14]=2)[CH2:9][NH:8][CH2:17]1

Participants

4

Reactant 1

HCID 695103884,4-Dimethyl-7-{2-[(2-methylamino-pyrimidin-4-ylmethyl)-amino]-benzoylamino}-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester

Product 1

HCID 10319738N-(4,4-Dimethyl-1,2,3,4-tetrahydro-isoquinolin-7-yl)-2-[(2-methylamino-pyrimidin-4-ylmethyl)-amino]-benzamide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

4,4-Dimethyl-7-{2-[(2-methylamino-pyrimidin-4-ylmethyl)-amino]-benzoylamino}-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester (Step D, 0.65 g, 1.26 mmol) in 10 mL of 50% of TFA in CH2Cl2 was stirred at RT for 1 h. The volatiles were removed under reduced pressure, the residue was purified by flash column chromatography, and the titled compound was obtained as a white solid. MS (ES+): 417.1 (M+H)+. Calc'd for C24H28N6O-416.52.

Workup

  1. customThe volatiles were removed under reduced pressure
  2. customthe residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-df425e46e7234318ac66ebacf7e4b40d
Source dataset
uspto-grants-2007_12
Patent number
US07307088B2

Reaction notes

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