Diclofensine → Tartrate

HRID 2403969

Reaction equation

ClC1C=C(C2C3C(=CC(OC)=CC=3)CN(C)C2)C=CC=1Cl.[C:22]([C@@H:25]([C@H:27]([C:29]([OH:31])=[O:30])[OH:28])[OH:26])([OH:24])=[O:23].[N:32]1[CH:33]=[N:34][N:35]2[CH:40]=[C:39]([C:41]3[CH:50]=[C:49]4[C:44]([CH:45]([C:51]5[CH:56]=[CH:55][C:54]([Cl:57])=[C:53]([Cl:58])[CH:52]=5)[CH2:46][NH:47][CH2:48]4)=[CH:43][CH:42]=3)[CH:38]=[CH:37][C:36]=12>>[C:22]([C@@H:25]([C@H:27]([C:29]([O-:31])=[O:30])[OH:28])[OH:26])([O-:24])=[O:23].[C:22]([C@@H:25]([C@H:27]([C:29]([OH:31])=[O:30])[OH:28])[OH:26])([OH:24])=[O:23].[N:32]1[CH:33]=[N:34][N:35]2[CH:40]=[C:39]([C:41]3[CH:50]=[C:49]4[C:44]([CH:45]([C:51]5[CH:56]=[CH:55][C:54]([Cl:57])=[C:53]([Cl:58])[CH:52]=5)[CH2:46][NH:47][CH2:48]4)=[CH:43][CH:42]=3)[CH:38]=[CH:37][C:36]=12

Participants

Reactant 2

HCID 68871Diclofensine

HCID 1177290427-([1,2,4]triazolo[1,5-a]pyridin-6-yl)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydroisoquinoline, L-Tartrate Salt

Product 2

HCID 119400Tartrate

HCID 1177290427-([1,2,4]triazolo[1,5-a]pyridin-6-yl)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydroisoquinoline, L-Tartrate Salt

Procedure

The L-tartrate of the (−)-7-([1,2,4]triazolo[1,5-a]pyridin-6-yl)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydroisoquinoline was prepared using (−)-4-(3,4-dichlorophenyl)-7-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline following similar steps described for the synthesis of the (+)-7-([1,2,4]triazolo[1,5-a]pyridin-6-yl)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydroisoquinoline, L-tartrate salt ([α]24D-6.0° (c 0.10, methanol)).

Sources & evidence

ORD record: ord-080f4c0bf0ee482c9143365b7c1908a0
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08802696B2

Linked notes

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