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

HRID 61560Notes

Reaction equation

HRID 61560 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]([NH:10][C:11]2[CH:12]=[C:13]([C:17]3[N:26]=[C:25]([NH:27][C:28]4[CH:29]=[C:30]5[C:34](=[CH:35][CH:36]=4)[N:33](C(OC(C)(C)C)=O)[N:32]=[CH:31]5)[C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[N:18]=3)[CH:14]=[CH:15][CH:16]=2)=[O:9])[CH2:4][CH2:3]1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH:33]1[C:34]2[C:30](=[CH:29][C:28]([NH:27][C:25]3[C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[N:18]=[C:17]([C:13]4[CH:12]=[C:11]([NH:10][C:8]([N:5]5[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]5)=[O:9])[CH:16]=[CH:15][CH:14]=4)[N:26]=3)=[CH:36][CH:35]=2)[CH:31]=[N:32]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59361848HCID 59361848, compound

Product 1

HCID 11950701N-(3-(4-(1H-indazol-5-ylamino)quinazolin-2-yl)phenyl)-4-methylpiperazine-1-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To tert-butyl 5-(2-(3-(1-methylpiperazine-4-carboxamido)phenyl)quinazolin-4-ylamino)-1H-indazole-1-carboxylate (165 mg, 0.22 mmol) was added a solution of 1:1 TFA:CH2Cl2 (6 mL) and stirred at RT for 2 h. The reaction mixture was concentrated in vacuo and left under high vacuum for several hours. The crude product was purified by prep HPLC (method 25-50_70 mins) to afford N-(3-(4-(1H-indazol-5-ylamino)quinazolin-2-yl)phenyl)-4-methylpiperazine-1-carboxamide. (88 mg, 69%)

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. waitleft under high vacuum for several hours
  3. customThe crude product was purified by prep HPLC (method 25-50_70 mins)

Sources & evidence

ORD record
ord-7a2f52a1df7846c5b8c40b41e3b665c7
Source dataset
uspto-grants-2016_09
Patent number
US09440961B2

Reaction notes

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