HCID 178463217, compound → HCID 178463218, compound

HRID 2053726Notes

Reaction equation

HRID 2053726 reaction equation
[F:1][C:2]1[CH:38]=[CH:37][C:5]([CH2:6][CH2:7][NH:8][C:9](=[N:11][C:12]2[CH:20]=[C:19]3[C:15]([CH2:16][C@@H:17]([OH:36])[C@@H:18]3[NH:21][C:22]([C:24]3[CH:29]=[CH:28][C:27]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)=[CH:26][CH:25]=3)=[O:23])=[CH:14][CH:13]=2)[CH3:10])=[CH:4][CH:3]=1>CO>[OH2:23].[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][CH2:7][NH:8][C:9](=[N:11][C:12]2[CH:20]=[C:19]3[C:15]([CH2:16][C@@H:17]([OH:36])[C@@H:18]3[NH:21][C:22]([C:24]3[CH:29]=[CH:28][C:27]([C:30]4[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=4)=[CH:26][CH:25]=3)=[O:23])=[CH:14][CH:13]=2)[CH3:10])=[CH:37][CH:38]=1.[C:27]1([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH:26]=[CH:25][C:24]([C:22]([NH:21][C@@H:18]2[C:19]3[C:15](=[CH:14][CH:13]=[C:12]([N:11]=[C:9]([NH:8][CH2:7][CH2:6][C:5]4[CH:37]=[CH:38][C:2]([F:1])=[CH:3][CH:4]=4)[CH3:10])[CH:20]=3)[CH2:16][C@H:17]2[OH:36])=[O:23])=[CH:29][CH:28]=1

Participants

3

Reactant 1

HCID 178463217HCID 178463217, compound

Product 1

HCID 178463218HCID 178463218, compoundYield 112.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Add 21.8 L of methanol to 2.86 kg of biphenyl-4-carboxylic acid (R)-(6-(1-((4-fluorobenzyl)methylamino)ethylideneamino)-2(R)-hydroxyindan-1-yl)amide solvate. Pass the solution through a carbon impregnated filter and rinse the filter with 24 L of methanol. Add 5.7 kg of water to the solution over 35 min followed by 15 g of Biphenyl-4-carboxylic acid (R)-(6-(1-((4-fluorobenzyl)methylamino)ethylideneamino)-2(R)-hydroxyindan-1-yl)amide hemihydrate seed crystals. After 20 min, add 1.15 kg of water followed by 15 g of seed crystals. After 1 h, add another 1.15 kg of water over 30 min followed by 15 g of seed crystals. After 10 min, add 3.4 kg of water over 1 h and stir the slurry at room temperature for 1 h and at 0° C. for 45 min. Collect the solid by filtration, rinse with a cold solution of 11.4 L of methanol and 2.9 L of water, and dry to afford 2.19 kg of the title compound as a white solid.

Workup

  1. filtrationPass the solution through a carbon impregnated filter
  2. washrinse the
  3. filtrationfilter with 24 L of methanol
  4. additionAdd 5.7 kg of water to the solution over 35 min
  5. additionadd 1.15 kg of water
  6. waitAfter 1 h
  7. additionadd another 1.15 kg of water over 30 min
  8. waitAfter 10 min
  9. additionadd 3.4 kg of water over 1 h
  10. waitat 0° C. for 45 min
  11. customCollect the solid
  12. filtrationby filtration
  13. washrinse with a cold solution of 11.4 L of methanol and 2.9 L of water
  14. customdry

Sources & evidence

ORD record
ord-c68fe6f11904486a983de00e3b490abd
Source dataset
uspto-grants-2008_02
Patent number
US07326731B2

Reaction notes

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