Trifluoroacetic acid → 4-[(4-Amino-1-piperidinyl)methyl]-3-chloro-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-one

HRID 15303Notes

Reaction equation

HRID 15303 reaction equation
CC([N:5]([CH:9]1[CH2:14][CH2:13][N:12]([CH2:15][CH:16]2[C:20]3=[C:21]([Cl:29])[CH:22]=[N:23][C:24]4[CH:25]=[CH:26][C:27](=[O:28])[N:18]([C:19]=43)[CH2:17]2)[CH2:11][CH2:10]1)C(=O)[O-])(C)C.FC(F)(F)C(O)=O>ClCCl>[NH2:5][CH:9]1[CH2:14][CH2:13][N:12]([CH2:15][CH:16]2[C:20]3=[C:21]([Cl:29])[CH:22]=[N:23][C:24]4[CH:25]=[CH:26][C:27](=[O:28])[N:18]([C:19]=43)[CH2:17]2)[CH2:11][CH2:10]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 866305791,1-dimethylethyl{1-[(3-chloro-7-oxo-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-4-yl)methyl]-4-piperidinyl}carbamate

Product 1

HCID 577074754-[(4-Amino-1-piperidinyl)methyl]-3-chloro-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-oneYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A suspension of 1,1-dimethylethyl{1-[(3-chloro-7-oxo-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-4-yl)methyl]-4-piperidinyl}carbamate (1.475 g, 4.63 mmol) in dichloromethane (15 ml) was treated with trifluoroacetic acid (12 ml) and stirred at room temperature for 1 h. The reaction mixture was evaporated and then treated with aqueous sodium bicarbonate solution and a 4:1 dichloromethane:methanol solution. The aqueous phase was extracted about 15 times with a 4:1 dichloromethane:methanol solution and then the combined organic phases were dried and the solvent was removed. The residue was subjected to column chromatography on silica gel using a dichloromethane, methanol and aqueous ammonia gradient to provide the desired compound (0.94 g, 84%).

Workup

  1. customThe reaction mixture was evaporated
  2. additiontreated with aqueous sodium bicarbonate solution
  3. extractionThe aqueous phase was extracted about 15 times with a 4:1 dichloromethane
  4. dry with materialmethanol solution and then the combined organic phases were dried
  5. customthe solvent was removed

Sources & evidence

ORD record
ord-042d5e6616f44bccba2c60b373ec8837
Source dataset
uspto-grants-2010_06
Patent number
US07732461B2

Reaction notes

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