L-Tartaric acid → HCID 131733701, compound

HRID 706407Notes

Reaction equation

HRID 706407 reaction equation
O.[CH3:2][C@H:3]1[N:8]([CH2:9][C:10]([F:13])([F:12])[F:11])[C:7](=[O:14])[C@@H:6]([NH:15][C:16]([C:18]2[CH:19]=[C:20]3[CH2:35][C@@:25]4([C:33]5[C:28](=[N:29][CH:30]=[CH:31][CH:32]=5)[NH:27][C:26]4=[O:34])[CH2:24][C:21]3=[N:22][CH:23]=2)=[O:17])[CH2:5][C@H:4]1[C:36]1[C:41]([F:42])=[CH:40][CH:39]=[C:38]([F:43])[C:37]=1[F:44].[C:45]([OH:54])(=[O:53])[C@@H:46]([C@H:48]([C:50]([OH:52])=[O:51])[OH:49])[OH:47]>CC(CC(C)=O)C>[C:45]([OH:54])(=[O:53])[C@@H:46]([C@H:48]([C:50]([OH:52])=[O:51])[OH:49])[OH:47].[CH3:2][C@H:3]1[N:8]([CH2:9][C:10]([F:11])([F:12])[F:13])[C:7](=[O:14])[C@@H:6]([NH:15][C:16]([C:18]2[CH:19]=[C:20]3[CH2:35][C@@:25]4([C:33]5[C:28](=[N:29][CH:30]=[CH:31][CH:32]=5)[NH:27][C:26]4=[O:34])[CH2:24][C:21]3=[N:22][CH:23]=2)=[O:17])[CH2:5][C@H:4]1[C:36]1[C:41]([F:42])=[CH:40][CH:39]=[C:38]([F:43])[C:37]=1[F:44]

Participants

4

Reactant 2

HCID 444305L-Tartaric acidHCID 1180235871488325-98-9

Product 1

HCID 131733701HCID 131733701, compound

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent2×

Procedure

3 g of (S)—N-((3S,5S,6R)-6-methyl-2-oxo-1-(2,2,2-trifluoroethyl)-5-(2,3,6-trifluorophenyl)piperidin-3-yl)-2′-oxo-1′,2′,5,7-tetrahydrospiro[cyclopenta[b]pyridine-6,3′-pyrrolo[2,3-b]pyridine]-3-carboxamide monohydrate and 0.724 g of L-tartaric acid was slurried in 15 ml MIBK overnight yielding a thick suspension. 45 ml of additional MIBK was added and slurrying continued for another day. The solids were isolated and dried for 3 days under flowing nitrogen purge yielding crystalline (S)—N-((3S,5S,6R)-6-methyl-2-oxo-1-(2,2,2-trifluoroethyl)-5-(2,3,6-trifluorophenyl)piperidin-3-yl)-2′-oxo-1′,2′,5,7-tetrahydrospiro[cyclopenta[b]pyridine-6,3′-pyrrolo[2,3-b]pyridine]-3-carboxamide L-tartaric acid cocrystal form.

Workup

  1. customyielding a thick suspension
  2. waitslurrying continued for another day
  3. customThe solids were isolated
  4. customdried for 3 days under flowing nitrogen
  5. custompurge

Sources & evidence

ORD record
ord-462ce4fec10542d494e8912eed00557e
Source dataset
uspto-grants-2015_11
Patent number
US09174989B2

Reaction notes

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