Tetrafluoro-m-phenylenediamine dihydrochloride → (4r)-4-({4-[(2,3-Dihydro-1,4-benzodioxin-6-ylmethyl)amino]-1-piperidinyl}methyl)-3-fluoro-4,5-dihydro-7h-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-one dihydrochloride

HRID 15369

Reaction equation

HRID 15369 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([CH2:8][C@H:9]2[C:13]3=[C:14]([F: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]1[C:28]2[CH:29]=[CH:30][C:31]([CH:33]=O)=[CH:32][C:27]=2[O:26][CH2:25][CH2:24]1.C1(N)C(F)=C(F)C(F)=C(N)C=1F.[ClH:47].Cl>>[ClH:47].[ClH:47].[O:23]1[C:28]2[CH:29]=[CH:30][C:31]([CH2:33][NH:1][CH:2]3[CH2:7][CH2:6][N:5]([CH2:8][C@H:9]4[C:13]5=[C:14]([F:22])[CH:15]=[N:16][C:17]6[CH:18]=[CH:19][C:20](=[O:21])[N:11]([C:12]=65)[CH2:10]4)[CH2:4][CH2:3]3)=[CH:32][C:27]=2[O:26][CH2:25][CH2:24]1

Participants

4

Reactant 3

HCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 2481272,3-Dihydro-1,4-benzodioxin-6-carbaldehydeHCID 68686964(4R)-4-[(4-amino-1-piperidinyl)methyl]-3-fluoro-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-one

Product 1

HCID 68684837(4r)-4-({4-[(2,3-Dihydro-1,4-benzodioxin-6-ylmethyl)amino]-1-piperidinyl}methyl)-3-fluoro-4,5-dihydro-7h-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-one dihydrochlorideYield 71%

Procedure

The title compound was prepared from (4R)-4-[(4-amino-1-piperidinyl)methyl]-3-fluoro-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-one Enantiomer 1 and 2,3-dihydro-1,4-benzodioxin-6-carboxaldehyde (Aldrich) according to the general method of Example 2(h) (except that the dihydrochloride was prepared) in 71% yield.

Workup

  1. customwas prepared) in 71% yield

Sources & evidence

ORD record
ord-2ed63c1b192a4d2ead674ec3f2add09b
Source dataset
uspto-grants-2010_06
Patent number
US07732461B2

Linked notes

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