Hydrochloric Acid → 3-Chloro-4-({(3r,4s)-3-hydroxy-4-[([1,3]oxathiolo[5,4-c]pyridin-6-ylmethyl)amino]-1-piperidinyl}methyl)-4,5-dihydro-7h-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-one hydrochloride

HRID 15343

Reaction equation

HRID 15343 reaction equation
[NH2:1][C@H: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][C@H:3]1[OH:23].[S:24]1[C:32]2[CH:31]=[C:30]([CH:33]=O)[N:29]=[CH:28][C:27]=2[O:26][CH2:25]1.Cl.Cl.C(OCC)C>C(Cl)(Cl)Cl>[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][C@H:2]([NH:1][CH2:33][C:30]5[N:29]=[CH:28][C:27]6[O:26][CH2:25][S:24][C:32]=6[CH:31]=5)[C@H:3]([OH:23])[CH2:4]4)[C:13]=1[C:12]=23

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10953452Ether hydrochlorideHCID 59254367[1,3]Oxathiolo[5,4-c]pyridine-6-carbaldehydeHCID 68685696racemic 4-{[(3R,4S)-4-amino-3-hydroxy-1-piperidinyl]methyl}-3-chloro-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-one

Product 1

HCID 686880503-Chloro-4-({(3r,4s)-3-hydroxy-4-[([1,3]oxathiolo[5,4-c]pyridin-6-ylmethyl)amino]-1-piperidinyl}methyl)-4,5-dihydro-7h-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-one hydrochloride

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

The free base of the title compound was synthesised from racemic 4-{[(3R,4S)-4-amino-3-hydroxy-1-piperidinyl]methyl}-3-chloro-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-one and [1,3]oxathiolo[5,4-c]pyridine-6-carbaldehyde (for a synthesis see WO2004058144, Example 61) according to the general method of Example 24(b). The free base of the title compound was converted to the hydrochloride by dissolving in chloroform and adding 1 equivalent of 1M HCl/diethyl ether, then evaporating to dryness. MS as that of free base.

Workup

  1. customevaporating to dryness

Sources & evidence

ORD record
ord-8c3e57c2b7844e3fa5db393895f2250f
Source dataset
uspto-grants-2010_06
Patent number
US07732461B2

Linked notes

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