Trifluoroacetic acid → 1-(Benzo[d][1,3]dioxol-5-yl)-N-(2-tert-butyl-1-(1,3-dihydroxypropan-2-yl)indolin-5-yl)cyclopropanecarboxamide

HRID 1908549Notes

Reaction equation

HRID 1908549 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3([C:13]([NH:15][C:16]4[CH:17]=[C:18]5[C:22](=[CH:23][CH:24]=4)[NH:21][CH:20]([C:25]([CH3:28])([CH3:27])[CH3:26])[CH2:19]5)=[O:14])[CH2:12][CH2:11]3)=[CH:9][C:4]=2[O:3][CH2:2]1.F[C:30](F)(F)[C:31]([OH:33])=O.[C:36](O[BH-](OC(=O)C)OC(=O)C)(=[O:38])C.[Na+]>ClC(Cl)C.CC1(C)OCC(=O)CO1>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3([C:13]([NH:15][C:16]4[CH:17]=[C:18]5[C:22](=[CH:23][CH:24]=4)[N:21]([CH:30]([CH2:31][OH:33])[CH2:36][OH:38])[CH:20]([C:25]([CH3:28])([CH3:27])[CH3:26])[CH2:19]5)=[O:14])[CH2:12][CH2:11]3)=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 5049666Sodium triacetoxyborohydrideHCID 591292381-(Benzo[d][1,3]dioxol-5-yl)-N-(2-tert-butylindolin-5-yl)cyclopropanecarboxamide

Product 1

HCID 591294261-(Benzo[d][1,3]dioxol-5-yl)-N-(2-tert-butyl-1-(1,3-dihydroxypropan-2-yl)indolin-5-yl)cyclopropanecarboxamide

Reagents, catalysts & solvents 2

HCID 63651,1-DichloroethaneSolventHCID 27331412,2-Dimethyl-1,3-dioxan-5-oneSolvent

Procedure

1-(Benzo[d][1,3]dioxol-5-yl)-N-(2-tert-butylindolin-5-yl)cyclopropanecarboxamide (50 mg, 0.13 mmol) was dissolved in dichloroethane (0.20 mL) and 2,2-dimethyl-1,3-dioxan-5-one (0.20 mL). Trifluoroacetic acid was added (0.039 mL) and the resulting solution was allowed to stir for 20 minutes. Sodium triacetoxyborohydride was added (55 mg, 0.26 mmol) and the reaction mixture was stirred for 30 minutes. The crude reaction mixture was then evaporated to dryness, dissolved in N,N-dimethylformamide and purified by preparative HPLC using a gradient of 0-99% acetonitrile in water containing 0.05% trifluoroacetic acid.

Workup

  1. stirringthe reaction mixture was stirred for 30 minutes
  2. customThe crude reaction mixture
  3. customwas then evaporated to dryness
  4. dissolutiondissolved in N,N-dimethylformamide
  5. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-1042ba3a239942e29cd7b2012289a71e
Source dataset
uspto-grants-2013_12
Patent number
US08598181B2

Reaction notes

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