Trifluoroacetic acid → N-(3-(4-(1H-indazol-5-ylamino)quinazolin-2-yl)phenyl)-2-(4-methylpiperazin-1-yl)acetamide

HRID 1406907Notes

Reaction equation

HRID 1406907 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]([NH:11][C:12]2[CH:13]=[C:14]([C:18]3[N:27]=[C:26]([NH:28][C:29]4[CH:30]=[C:31]5[C:35](=[CH:36][CH:37]=4)[N:34](C(OC(C)(C)C)=O)[N:33]=[CH:32]5)[C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[N:19]=3)[CH:15]=[CH:16][CH:17]=2)=[O:10])[CH2:4][CH2:3]1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH:34]1[C:35]2[C:31](=[CH:30][C:29]([NH:28][C:26]3[C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[N:19]=[C:18]([C:14]4[CH:13]=[C:12]([NH:11][C:9](=[O:10])[CH2:8][N:5]5[CH2:4][CH2:3][N:2]([CH3:1])[CH2:7][CH2:6]5)[CH:17]=[CH:16][CH:15]=4)[N:27]=3)=[CH:37][CH:36]=2)[CH:32]=[N:33]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59361937tert-butyl 5-(2-(3-(2-(4-methylpiperazin-1-yl)acetamido)phenyl)quinazolin-4-ylamino)-1H-indazole-1-carboxylate

Product 1

HCID 59361877N-(3-(4-(1H-indazol-5-ylamino)quinazolin-2-yl)phenyl)-2-(4-methylpiperazin-1-yl)acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To tert-butyl 5-(2-(3-(2-(4-methylpiperazin-1-yl)acetamido)phenyl)-quinazolin-4-ylamino)-1H-indazole-1-carboxylate (22 mmol) was added a solution of 1:1 TFA:CH2Cl2 (2 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)-2-(4-methylpiperazin-1-yl)acetamide. (33 mg, 33%)

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-6b8f520791b247f38c540a9dc8bf2456
Source dataset
uspto-grants-2014_12
Patent number
US08916576B2

Reaction notes

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