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

HRID 15321Notes

Reaction equation

HRID 15321 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.[O:23]=[C:24]1[NH:29][C:28]2[CH:30]=[C:31]([CH:34]=O)[CH:32]=[CH:33][C:27]=2[O:26][CH2:25]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:31]5[CH:32]=[CH:33][C:27]6[O:26][CH2:25][C:24](=[O:23])[NH:29][C:28]=6[CH:30]=5)[CH2:3][CH2:4]4)[C:13]=1[C:12]=23

Participants

3

Reactant 2

HCID 107736383-oxo-3,4-dihydro-2H-1,4-benzoxazine-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 686856253-Chloro-4-[(4-{[(3-oxo-3,4-dihydro-2H-1,4-benzoxazin-6-yl)methyl]amino}-1-piperidinyl)methyl]-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-one HydrochlorideYield 69%

Procedure

The free base of the title compound was synthesised from 4-[(4-amino-1-piperidinyl)methyl]-3-chloro-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-one and 3-oxo-3,4-dihydro-2H-benzo[1,4]oxazine-6-carboxaldehyde (for a synthesis see WO2002056882, Example 5(b)), according to the general method of Example 2(h), in 69% yield.

Sources & evidence

ORD record
ord-d7c270c11b2d48df9ab6c3a0d6b5eae8
Source dataset
uspto-grants-2010_06
Patent number
US07732461B2

Reaction notes

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