FV-100 free base → HCID 56962118, compound

HRID 1775756Notes

Reaction equation

HRID 1775756 reaction equation
[NH2:1][C@@H:2]([CH:34]([CH3:36])[CH3:35])[C:3]([O:5][CH2:6][C@@H:7]1[C@@H:11]([OH:12])[CH2:10][C@H:9]([N:13]2[CH:18]=[C:17]3[CH:19]=[C:20]([C:22]4[CH:27]=[CH:26][C:25]([CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])=[CH:24][CH:23]=4)[O:21][C:16]3=[N:15][C:14]2=[O:33])[O:8]1)=[O:4].[ClH:37].CC(O)C>>[ClH:37].[NH2:1][CH:2]([CH:34]([CH3:35])[CH3:36])[C:3]([O:5][CH2:6][C@@H:7]1[C@@H:11]([OH:12])[CH2:10][C@H:9]([N:13]2[CH:18]=[C:17]3[CH:19]=[C:20]([C:22]4[CH:23]=[CH:24][C:25]([CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])=[CH:26][CH:27]=4)[O:21][C:16]3=[N:15][C:14]2=[O:33])[O:8]1)=[O:4]

Participants

3

Reactant 2

HCID 16063377FV-100 free baseHCID 21912024Isopropanol hydrochloride

Product 1

HCID 56962118HCID 56962118, compound

Procedure

The above reaction mixture from Example 15 was cooled below 5° C. and was added with 20% of HCl IPA solution until pH 1˜4. The mixture was stirred for additional 1 h and was filtered. The filter cake was washed with 34.6 kg of dichloromethane. Desired crude product was obtained. The overall yield from Example 12 was 67% and the purity was 97%. The crude product was recrystallized with methanol/dichloromethane/MTBE to give the desired pure product.

Workup

  1. temperaturewas cooled below 5° C.
  2. filtrationwas filtered
  3. washThe filter cake was washed with 34.6 kg of dichloromethane
  4. customDesired crude product was obtained
  5. customThe overall yield from Example 12
  6. customThe crude product was recrystallized with methanol/dichloromethane/MTBE
  7. customto give the desired pure product

Sources & evidence

ORD record
ord-34dff15e634d459f9e63aedea7ff38c8
Source dataset
uspto-grants-2016_02
Patent number
US09260469B2

Reaction notes

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