Trifluoroacetic acid → 2-[1-(2-Amino-pyrimidin-4-yl)-ethylamino]-N-(4,4-dimethyl-1,2,3,4-tetrahydro-isoquinolin-7-yl)-benzamide

HRID 969701Notes

Reaction equation

HRID 969701 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][CH:29]([C:31]3[CH:36]=[CH:35][N:34]=[C:33]([NH2:37])[N:32]=3)[CH3:30])=[CH:13][CH:14]=2)[CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O.[OH-].[Na+]>C(Cl)Cl>[NH2:37][C:33]1[N:32]=[C:31]([CH:29]([NH:28][C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=2[C:21]([NH:20][C:12]2[CH:11]=[C:10]3[C:15]([C:16]([CH3:19])([CH3:18])[CH2:17][NH:8][CH2:9]3)=[CH:14][CH:13]=2)=[O:38])[CH3:30])[CH:36]=[CH:35][N:34]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 59017468tert-Butyl 7-{2-[1-(2-amino-pyrimidin-4-yl)-ethylamino]-benzoylamino}-4,4-dimethyl-3,4-dihydro-1H-isoquinoline-2-carboxylate

Product 1

HCID 590174662-[1-(2-Amino-pyrimidin-4-yl)-ethylamino]-N-(4,4-dimethyl-1,2,3,4-tetrahydro-isoquinolin-7-yl)-benzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 7-{2-[1-(2-amino-pyrimidin-4-yl)-ethylamino]-benzoylamino}-4,4-dimethyl-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester (Example 125) (80 mg, 0.154 mmol) in CH2Cl2 (3 mL) was added TFA (2 mL). The resulting mixture was stirred at RT for 18 h and basified with 5 N NaOH and extracted with CH2Cl2 (2×15 mL). The combined organic layers were washed with saturated NaHCO3, water, brine, dried over MgSO4, and evaporated in vacuo to give the product. MS m/z: 417.5 (M+H). Calc'd. for C24H29N6O-417.51.

Workup

  1. extractionextracted with CH2Cl2 (2×15 mL)
  2. washThe combined organic layers were washed with saturated NaHCO3, water, brine
  3. dry with materialdried over MgSO4
  4. customevaporated in vacuo
  5. customto give the product

Sources & evidence

ORD record
ord-399d835161e0471faee77c8edbfb3428
Source dataset
uspto-grants-2007_12
Patent number
US07307088B2

Reaction notes

Loading…