Dichloromethane → 2-{4'-[(3Ar,6ar)-5-methylhexahydropyrrolo[3,4-b]pyrrol-1(2h)-yl]-1,1'-biphenyl-4-yl}pyridazin-3(2h)-one l-tartrate salt monohydrate

HRID 1947422Notes

Reaction equation

HRID 1947422 reaction equation
[C:1]([CH:4]([CH:6]([C:8]([OH:10])=[O:9])[OH:7])[OH:5])([OH:3])=[O:2].[CH3:11][N:12]1[CH2:19][C@@H:18]2[C@@H:14]([N:15]([C:20]3[CH:25]=[CH:24][C:23]([C:26]4[CH:31]=[CH:30][C:29]([N:32]5[C:37](=[O:38])[CH:36]=[CH:35][CH:34]=[N:33]5)=[CH:28][CH:27]=4)=[CH:22][CH:21]=3)[CH2:16][CH2:17]2)[CH2:13]1.ClCCl>O>[OH2:2].[C:1]([C@@H:4]([C@H:6]([C:8]([OH:10])=[O:9])[OH:7])[OH:5])([OH:3])=[O:2].[CH3:11][N:12]1[CH2:19][C@@H:18]2[C@@H:14]([N:15]([C:20]3[CH:25]=[CH:24][C:23]([C:26]4[CH:31]=[CH:30][C:29]([N:32]5[C:37](=[O:38])[CH:36]=[CH:35][CH:34]=[N:33]5)=[CH:28][CH:27]=4)=[CH:22][CH:21]=3)[CH2:16][CH2:17]2)[CH2:13]1

Participants

4

Reactant 2

HCID 6344DichloromethaneHCID 247439152-{4'-[(3aR,6aR)-5-Methylhexahydropyrrolo[3,4-b]pyrrol-1(2H)-yl]-1,1'-biphenyl-4-yl}pyridazin-3(2H)-one tartrate

Product 1

HCID 684946212-{4'-[(3Ar,6ar)-5-methylhexahydropyrrolo[3,4-b]pyrrol-1(2h)-yl]-1,1'-biphenyl-4-yl}pyridazin-3(2h)-one l-tartrate salt monohydrate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
48 °C

Procedure

2-{4′-[(3aR,6aR)-5-Methylhexahydropyrrolo[3,4-b]pyrrol-1(2H)-yl]-1,1′-biphenyl-4-yl}pyridazin-3(2H)-one tartrate (Form A) was suspended in 1 mL of solution mixture, which was prepared by mixing 5.0 mL of dichloromethane with 5.0 mL of 20% water (in methanol). The suspension was vortexed and heated to about 48° C. yielding a clear solution. The solution was then filtered and the supernatant cooled to ambient temperatures naturally overnight. The solids precipitated over the night were dissolved again the next day by heating the suspension to about 90° C. The solution was cooled slowly by progressively lowering the temperature of the water bath to ambient temperatures. Single crystals were offered.

Workup

  1. customwas prepared
  2. customyielding a clear solution
  3. filtrationThe solution was then filtered
  4. temperaturethe supernatant cooled to ambient temperatures naturally overnight
  5. customThe solids precipitated over the night
  6. dissolutionwere dissolved again the next day
  7. temperatureby heating the suspension to about 90° C
  8. temperatureThe solution was cooled slowly

Sources & evidence

ORD record
ord-c77efc41185f4df3b758028c9d078d57
Source dataset
uspto-grants-2013_03
Patent number
US08399468B2

Reaction notes

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