8-Fluoro-2,3-dihydro-1,4-benzodioxin-6-carboxaldehyde → 3-Chloro-4-[(4-{[(8-fluoro-2,3-dihydro-1,4-benzodioxin-6-yl)methyl]amino}-1-piperidinyl)methyl]-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-one Hydrochloride

HRID 15309Notes

Reaction equation

HRID 15309 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH:9]2[C:13]3=[C:14]([Cl:22])[CH:15]=[N:16][C:17]4[CH:18]=[CH:19][C:20](=[O:21])[N:11]([C:12]=43)[CH2:10]2)[CH2:4][CH2:3]1.[F:23][C:24]1[C:29]2[O:30][CH2:31][CH2:32][O:33][C:28]=2[CH:27]=[C:26]([CH:34]=O)[CH:25]=1>>[ClH:22].[Cl:22][C:14]1[CH:15]=[N:16][C:17]2[CH:18]=[CH:19][C:20](=[O:21])[N:11]3[CH2:10][CH:9]([CH2:8][N:5]4[CH2:6][CH2:7][CH:2]([NH:1][CH2:34][C:26]5[CH:25]=[C:24]([F:23])[C:29]6[O:30][CH2:31][CH2:32][O:33][C:28]=6[CH:27]=5)[CH2:3][CH2:4]4)[C:13]=1[C:12]=23

Participants

3

Reactant 2

HCID 574231098-Fluoro-2,3-dihydro-1,4-benzodioxin-6-carboxaldehydeHCID 577074754-[(4-Amino-1-piperidinyl)methyl]-3-chloro-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-one

Product 1

HCID 686849793-Chloro-4-[(4-{[(8-fluoro-2,3-dihydro-1,4-benzodioxin-6-yl)methyl]amino}-1-piperidinyl)methyl]-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-one HydrochlorideYield 56%

Procedure

The free base of the title compound was prepared from 4-[(4-amino-1-piperidinyl)methyl]-3-chloro-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-one (32 mg) and 8-fluoro-2,3-dihydro-1,4-benzodioxin-6-carboxaldehyde (18.2 mg) according to the general method of Example 2(h) in 56% yield.

Sources & evidence

ORD record
ord-e041b4d3eddd4e24b6e74471c998eb0a
Source dataset
uspto-grants-2010_06
Patent number
US07732461B2

Reaction notes

Loading…