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

HRID 61564Notes

Reaction equation

HRID 61564 reaction equation
[CH2:1]([NH:8][C:9](=[O:44])[NH:10][C:11]1[CH:12]=[C:13]([C:17]2[N:26]=[C:25]([NH:27][C:28]3[CH:29]=[C:30]4[C:34](=[CH:35][CH:36]=3)[N:33](C(OC(C)(C)C)=O)[N:32]=[CH:31]4)[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[N:18]=2)[CH:14]=[CH:15][CH:16]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH: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:9]([NH:8][CH2:1][C:2]5[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=5)=[O:44])[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 59361946tert-butyl 5-(2-(3-(3-benzylureido)phenyl)quinazolin-4-ylamino)-1H-indazole-1-carboxylate

Product 1

HCID 593618621-(3-(4-(1H-indazol-5-ylamino)quinazolin-2-yl)phenyl)-3-benzylurea

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To tert-butyl 5-(2-(3-(3-benzylureido)phenyl)quinazolin-4-ylamino)-1H-indazole-1-carboxylate (30 mg, 0.051 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 left under high vacuum for several hours. The crude product was triturated with ethyl ether to afford 1-(3-(4-(1H-indazol-5-ylamino)quinazolin-2-yl)phenyl)-3-benzylurea. (25 mg, 100%)

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

Sources & evidence

ORD record
ord-af1378305e2540709d2651ca7bf2d2a5
Source dataset
uspto-grants-2016_09
Patent number
US09440961B2

Reaction notes

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