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

HRID 1406913Notes

Reaction equation

HRID 1406913 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-a695738a591c404883571606003ad7c6
Source dataset
uspto-grants-2014_12
Patent number
US08916576B2

Reaction notes

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