Trifluoroacetic acid methylene chloride → N-(4,4-dimethyl-1,2,3,4-tetrahydro-isoquinolin-7-yl)-2-[(1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)-amino]-benzamide

HRID 969679Notes

Reaction equation

HRID 969679 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:39])[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[NH:28][CH2:29][C:30]3[C:38]4[C:33](=[N:34][CH:35]=[CH:36][CH:37]=4)[NH:32][CH: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:39])[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[NH:28][CH2:29][C:30]3[C:38]4[C:33](=[N:34][CH:35]=[CH:36][CH:37]=4)[NH:32][CH:31]=3)=[CH:13][CH:14]=2)[CH2:9][NH:8][CH2:17]1

Participants

3

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 695113924,4-Dimethyl-7-{2-[(1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)-amino]-benzoylamino}-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester

Product 1

HCID 59017450N-(4,4-dimethyl-1,2,3,4-tetrahydro-isoquinolin-7-yl)-2-[(1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)-amino]-benzamide

Procedure

4,4-Dimethyl-7-{2-[(1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)-amino]-benzoylamino}-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester (Step B, 0.45 g, 0.86 mmol) was treated with 10 mL of 1/1 TFA/CH2Cl2 solution and stirred at RT for 1 h. The volatiles were removed under reduced pressure and the residue was purified by flash column chromatography to obtain the titled compound as a white solid. MS (ES+): 426.1 (M+H)+. Calc'd for C26H27N5O-425.22.

Workup

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

Sources & evidence

ORD record
ord-5aafba399ec245e7ae4c0df7f31bed0e
Source dataset
uspto-grants-2007_12
Patent number
US07307088B2

Reaction notes

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