Trifluoroacetic acid → 4-(5-Cyano-7-isopropyl-1,3-benzoxazol-2-yl)-N-(pyrrolidin-3-ylmethyl)benzamide

HRID 2066833Notes

Reaction equation

HRID 2066833 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:34]([CH3:36])[CH3:35])[C:6]2[O:10][C:9]([C:11]3[CH:32]=[CH:31][C:14]([C:15]([NH:17][CH2:18][CH:19]4[CH2:23][CH2:22][N:21](C(OC(C)(C)C)=O)[CH2:20]4)=[O:16])=[CH:13][CH:12]=3)=[N:8][C:7]=2[CH:33]=1)#[N:2].FC(F)(F)C(O)=O>ClCCl>[C:1]([C:3]1[CH:4]=[C:5]([CH:34]([CH3:36])[CH3:35])[C:6]2[O:10][C:9]([C:11]3[CH:12]=[CH:13][C:14]([C:15]([NH:17][CH2:18][CH:19]4[CH2:23][CH2:22][NH:21][CH2:20]4)=[O:16])=[CH:31][CH:32]=3)=[N:8][C:7]=2[CH:33]=1)#[N:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68409608tert-Butyl 3-({[4-(5-cyano-7-isopropyl-1,3-benzoxazol-2-yl)benzoyl]amino}methyl)pyrrolidine-1-carboxylate

Product 1

HCID 684078314-(5-Cyano-7-isopropyl-1,3-benzoxazol-2-yl)-N-(pyrrolidin-3-ylmethyl)benzamideYield 90.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 3-({[4-(5-cyano-7-isopropyl-1,3-benzoxazol-2-yl)benzoyl]amino}methyl)pyrrolidine-1-carboxylate (910 mg) in dichloromethane (75 ml) was added 20 ml of trifluoroacetic acid. The mixture was stirred at room temperature for 2 h, and then concentrated in vacuo. The residue was basified by the addition of 75 ml of saturated aqueous sodium bicarbonate and diluted with 75 ml of ethyl acetate. The solids were filtered from both layers and dried in vacuo to provide the title compound (655 mg, 90%). Mass spectrum (ESI) 389.9 (M+1).

Workup

  1. concentrationconcentrated in vacuo
  2. additionThe residue was basified by the addition of 75 ml of saturated aqueous sodium bicarbonate
  3. additiondiluted with 75 ml of ethyl acetate
  4. filtrationThe solids were filtered from both layers
  5. customdried in vacuo

Sources & evidence

ORD record
ord-8d395143746b4045b5c7d3abdcf8823f
Source dataset
uspto-grants-2012_10
Patent number
US08293721B2

Reaction notes

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