Trifluoroacetic acid → 3-(3-(4-(1H-indazol-5-ylamino)quinazolin-2-yl)phenyl)-1,1-dimethylurea

HRID 61562Notes

Reaction equation

HRID 61562 reaction equation
[CH3:1][N:2]([CH3:39])[C:3](=[O:38])[NH:4][C:5]1[CH:6]=[C:7]([C:11]2[N:20]=[C:19]([NH:21][C:22]3[CH:23]=[C:24]4[C:28](=[CH:29][CH:30]=3)[N:27](C(OC(C)(C)C)=O)[N:26]=[CH:25]4)[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[N:12]=2)[CH:8]=[CH:9][CH:10]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH:27]1[C:28]2[C:24](=[CH:23][C:22]([NH:21][C:19]3[C:18]4[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=4)[N:12]=[C:11]([C:7]4[CH:6]=[C:5]([NH:4][C:3](=[O:38])[N:2]([CH3:1])[CH3:39])[CH:10]=[CH:9][CH:8]=4)[N:20]=3)=[CH:30][CH:29]=2)[CH:25]=[N:26]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59361984HCID 59361984, compound

Product 1

HCID 119507023-(3-(4-(1H-indazol-5-ylamino)quinazolin-2-yl)phenyl)-1,1-dimethylurea

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To tert-butyl 5-(2-(3-(3,3-dimethylureido)phenyl)quinazolin-4-ylamino)-1H-indazole-1-carboxylate (50 mg, 0.10 mmol) was added a solution of 1:1 TFA:CH2Cl2 (3 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 triturated with ethyl ether and the yellow solid was purified by prep HPLC (method 25-50_70 mins) to afford 3-(3-(4-(1H-indazol-5-ylamino)quinazolin-2-yl)phenyl)-1,1-dimethylurea. (36 mg, 86%)

Workup

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

Sources & evidence

ORD record
ord-9e773fccc64c481588938d04683dfa4e
Source dataset
uspto-grants-2016_09
Patent number
US09440961B2

Reaction notes

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