Trifluoroacetic acid → 1-(4-Amino-quinazolin-7-ylmethyl)-4-(1H-pyrrolo[3,2-c]pyridin-2-ylmethyl)-piperazin-2-one

HRID 1432967Notes

Reaction equation

HRID 1432967 reaction equation
C(OC([N:8]1[C:16]2[CH:15]=[CH:14][N:13]=[CH:12][C:11]=2[CH:10]=[C:9]1[CH2:17][N:18]1[CH2:23][CH2:22][N:21]([CH2:24][C:25]2[CH:34]=[C:33]3[C:28]([C:29]([NH2:35])=[N:30][CH:31]=[N:32]3)=[CH:27][CH:26]=2)[C:20](=[O:36])[CH2:19]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:35][C:29]1[C:28]2[C:33](=[CH:34][C:25]([CH2:24][N:21]3[CH2:22][CH2:23][N:18]([CH2:17][C:9]4[NH:8][C:16]5[CH:15]=[CH:14][N:13]=[CH:12][C:11]=5[CH:10]=4)[CH2:19][C:20]3=[O:36])=[CH:26][CH:27]=2)[N:32]=[CH:31][N:30]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 538741592-[4-(4-Amino-quinazolin-7-ylmethyl)-3-oxo-piperazin-1-ylmethyl]-pyrrolo[3,2-c]pyridine-1-carboxylic acid tert-butyl ester

Product 1

HCID 539048461-(4-Amino-quinazolin-7-ylmethyl)-4-(1H-pyrrolo[3,2-c]pyridin-2-ylmethyl)-piperazin-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution containing 2-[4-(4-amino-quinazolin-7-ylmethyl)-3-oxo-piperazin-1-ylmethyl]-pyrrolo[3,2-c]pyridine-1-carboxylic acid tert-butyl ester (50 mg, 0.12 mmol) in CH2Cl2 (5 mL is added TFA (1 mL) at ambient temperature. After 16 h, the reaction mixture is concentrated to dryness, diluted with water and purified by reverse-phase HPLC [Buffer A: water w/0.1% TFA; Buffer B: CH3CN w/0.1% TFA; Gradient: 0% B to 45% B over 30 min] to provide 34 mg (73%, two steps) of the title compound as a white, lyophilized solid. 1H NMR (300 MHz, CDCl3) δ2.77 (s, 3H), 3.23 (s, 2H), 3.31 (m, 2H), 3.89 (s, 2H), 4.00 (br s, 3H), 4.71 (s, 2H), 6.94 (s, 1H), 7.60 (m, 2H), 7.84 (d, J=6.5 Hz, 1H), 8.36 (m, 2H), 8.81 (s, 1H), 9.18 (s, 1H), 9.73 (br s, 2H), 12.87 (s, 1H) ppm; MS (ion spray): m/z 388 (M+H).

Workup

  1. concentrationthe reaction mixture is concentrated to dryness
  2. additiondiluted with water
  3. custompurified by reverse-phase HPLC [Buffer A: water

Sources & evidence

ORD record
ord-4933038d5c6e479593b446bb73b624e5
Source dataset
uspto-grants-2009_11
Patent number
US07612075B2

Reaction notes

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