Trifluoroacetic acid → N-(3-(4-(1H-indazol-5-ylamino)quinazolin-2-yl)phenyl)-3-(4-isopropyl piperazin-1-yl)propanamide

HRID 61553Notes

Reaction equation

HRID 61553 reaction equation
[CH:1]([N:4]1[CH2:9][CH2:8][N:7]([CH2:10][CH2:11][C:12]([NH:14][C:15]2[CH:16]=[C:17]([C:21]3[N:30]=[C:29]([NH:31][C:32]4[CH:33]=[C:34]5[C:38](=[CH:39][CH:40]=4)[N:37](C(OC(C)(C)C)=O)[N:36]=[CH:35]5)[C:28]4[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=4)[N:22]=3)[CH:18]=[CH:19][CH:20]=2)=[O:13])[CH2:6][CH2:5]1)([CH3:3])[CH3:2].C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH:37]1[C:38]2[C:34](=[CH:33][C:32]([NH:31][C:29]3[C:28]4[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=4)[N:22]=[C:21]([C:17]4[CH:16]=[C:15]([NH:14][C:12](=[O:13])[CH2:11][CH2:10][N:7]5[CH2:6][CH2:5][N:4]([CH:1]([CH3:2])[CH3:3])[CH2:9][CH2:8]5)[CH:20]=[CH:19][CH:18]=4)[N:30]=3)=[CH:40][CH:39]=2)[CH:35]=[N:36]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59361908tert-butyl 5-(2-(3-(3-(4-isopropylpiperazin-1-yl)propanamido)phenyl)quinazolin-4-ylamino)-1H-indazole-1-carboxylate

Product 1

HCID 11950893N-(3-(4-(1H-indazol-5-ylamino)quinazolin-2-yl)phenyl)-3-(4-isopropyl piperazin-1-yl)propanamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To tert-butyl 5-(2-(3-(3-(4-isopropylpiperazin-1-yl)propanamido)phenyl)-quinazolin-4-ylamino)-1H-indazole-1-carboxylate (60 mg, 0.094 mmol) was added a solution of 1:1 TFA:CH2Cl2 (4 mL) and stirred at RT for 2 h. The reaction mixture was concentrated in vacuo and the crude product was purified by prep HPLC (method 10-35_90 mins) to afford N-(3-(4-(1H-indazol-5-ylamino)quinazolin-2-yl)phenyl)-3-(4-isopropylpiperazin-1-yl)propanamide. (61 mg, 0.11 mmol, 100%).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe crude product was purified by prep HPLC (method 10-35_90 mins)

Sources & evidence

ORD record
ord-576a956430014cf398648c48c230fb95
Source dataset
uspto-grants-2016_09
Patent number
US09440961B2

Reaction notes

Loading…