Trifluoroacetic acid → HCID 25011914, compound

HRID 1407005Notes

Reaction equation

HRID 1407005 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([NH:29][C:30]3[CH:31]=[C:32]4[C:36](=[CH:37][CH:38]=3)[N:35](C(OC(C)(C)C)=O)[N:34]=[CH:33]4)=[N:8][C:9]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([NH:19][C:20](=[O:28])[CH2:21][N:22]4[CH2:27][CH2:26][O:25][CH2:24][CH2:23]4)[CH:14]=3)=[N:10]2)=[CH:5][C:4]=1[O:46][CH2:47][CH2:48][N:49]1[CH2:53][CH2:52][CH2:51][CH2:50]1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH:35]1[C:36]2[C:32](=[CH:31][C:30]([NH:29][C:7]3[C:6]4[C:11](=[CH:12][C:3]([O:2][CH3:1])=[C:4]([O:46][CH2:47][CH2:48][N:49]5[CH2:53][CH2:52][CH2:51][CH2:50]5)[CH:5]=4)[N:10]=[C:9]([C:13]4[CH:14]=[C:15]([NH:19][C:20](=[O:28])[CH2:21][N:22]5[CH2:23][CH2:24][O:25][CH2:26][CH2:27]5)[CH:16]=[CH:17][CH:18]=4)[N:8]=3)=[CH:38][CH:37]=2)[CH:33]=[N:34]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59361966HCID 59361966, compound

Product 1

HCID 25011914HCID 25011914, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of tert-butyl 5-(7-methoxy-2-(3-(2-morpholinoacetamido)-phenyl)-6-(2-(pyrrolidin-1-yl)ethoxy)quinazolin-4-ylamino)-1H-indazole-1-carboxylate (0.085 g, 0.118 mmol) in CH2Cl2 (4 mL) was added TFA (6 mL). The resultant mixture was stirred at RT for 1.25 h, upon which the volatiles were removed in vacuo and the residue was triturated with Et2O to give N-(3-(4-(1H-indazol-5-ylamino)-7-methoxy-6-(2-(pyrrolidin-1-yl)ethoxy)quinazolin-2-yl)phenyl)-2-morpholinoacetamide (0.090 g, 0.112 mmol, 95%). MS 623.2 (M+1). HPLC retention time 3.806 mins.

Workup

  1. customwere removed in vacuo
  2. customthe residue was triturated with Et2O

Sources & evidence

ORD record
ord-092496a7daee4a72adc161b755f7adba
Source dataset
uspto-grants-2014_12
Patent number
US08916576B2

Reaction notes

Loading…