Trifluoroacetic acid → HCID 57732997, compound

HRID 1891298Notes

Reaction equation

HRID 1891298 reaction equation
C(O)(C(F)(F)F)=O.[F:8][C:9]1([F:49])[O:13][C:12]2[CH:14]=[CH:15][C:16]([C:18]3([C:21]([NH:23][C:24]4[N:25]=[C:26]([C:34]5[CH:35]=[C:36]([CH:46]=[CH:47][CH:48]=5)[CH2:37][NH:38]C(=O)OC(C)(C)C)[C:27]5[C:32]([CH:33]=4)=[CH:31][CH:30]=[CH:29][CH:28]=5)=[O:22])[CH2:20][CH2:19]3)=[CH:17][C:11]=2[O:10]1>C(Cl)Cl.[OH-].[Na+]>[NH2:38][CH2:37][C:36]1[CH:35]=[C:34]([C:26]2[C:27]3[C:32](=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH:33]=[C:24]([NH:23][C:21]([C:18]3([C:16]4[CH:15]=[CH:14][C:12]5[O:13][C:9]([F:49])([F:8])[O:10][C:11]=5[CH:17]=4)[CH2:19][CH2:20]3)=[O:22])[N:25]=2)[CH:48]=[CH:47][CH:46]=1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57733020HCID 57733020, compound

Product 1

HCID 57732997HCID 57732997, compoundYield 100.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 14798Sodium HydroxideSolvent

Procedure

TFA (500 μL) was added to a solution of tert-butyl 3-(3-(1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamido)isoquinolin-1-yl)benzylcarbamate (115 mg, 0.200 mmol) in CH2Cl2 (1.5 mL). The reaction was stirred at room temperature for 1 hour. The reaction was diluted with CH2Cl2 and 1N NaOH was added until the mixture become basic. The organic layer was dried over MgSO4, filtered and concentrated to yield N-(1-(3-(Aminomethyl)phenyl)isoquinolin-3-yl)-1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamide as a white solid (95 mg, 99%). ESI-MS m/z calc. 473.2. found 474.2 (M+1)+. Retention time 1.62 minutes.

Workup

  1. additionwas added until the mixture
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-f2b41b12322640ab8360778b1adc39a7
Source dataset
uspto-grants-2013_08
Patent number
US08507524B2

Reaction notes

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