7-Chloro-3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine-6-carbaldehyde → 3-Chloro-4-[(4-{[(7-chloro-3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)methyl]amino}-1-piperidinyl)methyl]4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-one Hydrochloride

HRID 15306Notes

Reaction equation

HRID 15306 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.[Cl:23][C:24]1[C:33]([CH:34]=O)=[N:32][C:31]2[NH:30][C:29](=[O:36])[CH2:28][O:27][C:26]=2[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:33]5[C:24]([Cl:23])=[CH:25][C:26]6[O:27][CH2:28][C:29](=[O:36])[NH:30][C:31]=6[N:32]=5)[CH2:3][CH2:4]4)[C:13]=1[C:12]=23

Participants

3

Reactant 2

HCID 574868727-Chloro-3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine-6-carbaldehydeHCID 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 686842043-Chloro-4-[(4-{[(7-chloro-3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)methyl]amino}-1-piperidinyl)methyl]4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-one HydrochlorideYield 84%

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 (75 mg) and 7-chloro-3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine-6-carboxaldehyde (for a synthesis see WO2003064421, Example 15(c)) (50 mg) according to the general method of Example 2(h) in 84% yield.

Sources & evidence

ORD record
ord-73c74793dde84906b9bd3178e4de880d
Source dataset
uspto-grants-2010_06
Patent number
US07732461B2

Reaction notes

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