2-Chloro-4-hydroxybenzoic acid hydrate → (R)-1,3,4,10b-tetrahydro-7-methylthio-pyrazino[2,1-a]isoindol-6(2H)-one hydrochloric acid salt

HRID 1296245Notes

Reaction equation

HRID 1296245 reaction equation
O.[Cl:2]C1C=C(O)C=CC=1C(O)=O.C(OC([N:20]1[CH2:35][CH2:34][N:23]2[C:24](=[O:33])[C:25]3[C:30]([CH:22]2[CH2:21]1)=[CH:29][CH:28]=[CH:27][C:26]=3[S:31][CH3:32])=O)(C)(C)C.C(OC(N1CCN2C(=O)C3C(C2C1)=CC(OC)=CC=3Cl)=O)(C)(C)C>>[ClH:2].[CH3:32][S:31][C:26]1[CH:27]=[CH:28][CH:29]=[C:30]2[C:25]=1[C:24](=[O:33])[N:23]1[CH2:34][CH2:35][NH:20][CH2:21][C@H:22]12

Participants

4

Reactant 3

HCID 533954432-Chloro-4-hydroxybenzoic acid hydrateHCID 68688757(+/-)-N-(t-butoxycarbonyl)-1,3,4,10b-tetrahydro-7-chloro-9-methoxy-pyrazino[2,1-a]isoindol-6(2H)-oneHCID 68691317(+/-)-N-(t-butoxycarbonyl)-1,3,4,10b-tetrahydro-7-methylthio-pyrazino[2,1-a]isoindol-6(2H)-one

Product 1

HCID 11402999(R)-1,3,4,10b-tetrahydro-7-methylthio-pyrazino[2,1-a]isoindol-6(2H)-one hydrochloric acid salt

Procedure

Prepared according to procedures described in Examples 59 and 60 with substitution of 2-(methylthio)benzoic acid for 2-chloro-4-hydroxybenzoic acid hydrate in Example 59, Step A, and (±)-N-(t-butoxycarbonyl)-1,3,4,10b-tetrahydro-7-methylthio-pyrazino[2,1-a]isoindol-6(2H)-one (Example 45) for (±)-N-(t-butoxycarbonyl)-1,3,4,10b-tetrahydro-7-chloro-9-methoxy-pyrazino[2,1-a]isoindol-6(2H)-one in Example 60, Step A. MS (ESI) 235.2 (M−Cl).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-27724c4bc4ea4b4b81cbc464ac103c5d
Source dataset
uspto-grants-2007_07
Patent number
US07244843B2

Reaction notes

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