Hydrochloric Acid → (4R/S)-4-({4-amino-1-piperidinyl}methyl)-3,4-difluoro-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-one dihydrochloride

HRID 15165Notes

Reaction equation

HRID 15165 reaction equation
[F:1][C:2]1[CH:3]=[N:4][C:5]2[CH:6]=[CH:7][C:8](=[O:30])[N:9]3[CH2:13][C:12]([CH2:15][N:16]4[CH2:21][CH2:20][CH:19]([NH:22]C(=O)OC(C)(C)C)[CH2:18][CH2:17]4)([F:14])[C:11]=1[C:10]=23.[ClH:31].O1CCOCC1>ClCCl.CO>[ClH:31].[ClH:31].[NH2:22][CH:19]1[CH2:18][CH2:17][N:16]([CH2:15][C:12]2([F:14])[C:11]3=[C:2]([F:1])[CH:3]=[N:4][C:5]4[CH:6]=[CH:7][C:8](=[O:30])[N:9]([C:10]=43)[CH2:13]2)[CH2:21][CH2:20]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 1317281671,1-Dimethylethyl {1-[((4R/S)-3,4-difluoro-7-oxo-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-4-yl)methyl]-4-piperidinyl}carbamate

Product 1

HCID 131728168(4R/S)-4-({4-amino-1-piperidinyl}methyl)-3,4-difluoro-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-one dihydrochloride

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 1,1-dimethylethyl {1-[((4R/S)-3,4-difluoro-7-oxo-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-4-yl)methyl]-4-piperidinyl}carbamate (98 mg, 0.23 mmol) in dichloromethane (2 ml) and methanol (1.5 ml), was treated with hydrochloric acid in 1,4-dioxane (4M, 3.5 ml, 14 mmol). After 1.5 hours the mixture was evaporated affording the product (82 mg).

Workup

  1. customAfter 1.5 hours the mixture was evaporated

Sources & evidence

ORD record
ord-3aea0df95d4d496985ba3534469d3cbe
Source dataset
uspto-grants-2010_06
Patent number
US07732460B2

Reaction notes

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