Methylorthoformate → HCID 86725393, compound

HRID 1503840Notes

Reaction equation

HRID 1503840 reaction equation
[C:1]([C:4]1[C:5]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([N:21]3[CH2:26][CH2:25][N:24]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:23][CH2:22]3)=[CH:17][C:16]=2[F:34])=[N:6][C:7]([S:12][CH3:13])=[N:8][C:9]=1[NH:10][NH2:11])(=[O:3])[NH2:2].[CH:35]([O-])([O-])OC>CC(N(C)C)=O>[C:1]([C:4]1[C:9]2[N:8]([CH:35]=[N:11][N:10]=2)[C:7]([S:12][CH3:13])=[N:6][C:5]=1[NH:14][C:15]1[CH:20]=[CH:19][C:18]([N:21]2[CH2:22][CH2:23][N:24]([C:27]([O:29][C:30]([CH3:31])([CH3:33])[CH3:32])=[O:28])[CH2:25][CH2:26]2)=[CH:17][C:16]=1[F:34])(=[O:3])[NH2:2]

Participants

4

Reactant 2

HCID 53629101MethylorthoformateHCID 86725391HCID 86725391, compound

Product 1

HCID 86725393HCID 86725393, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of the product of Example 28D (240 mg, 0.5 mmol) in dimethylacetamide (2 mL) was added methyl orthoformate (2 mL). The mixture was stirred at ambient temperature for 1 hour and at 60° C. for 4 hours. After cooling to ambient temperature, petroleum 9/1 ether/ethyl acetate (50 mL) was added and the precipitate was filtered. The solid was washed with petroleum ether and dried under vacuum to give the title compound. MS: 503 (M+H+).

Workup

  1. temperatureAfter cooling to ambient temperature
  2. filtrationthe precipitate was filtered
  3. washThe solid was washed with petroleum ether
  4. customdried under vacuum

Sources & evidence

ORD record
ord-afc6e257e8ba4342ac1724e564d166d1
Source dataset
uspto-grants-2015_12
Patent number
US09212192B2

Reaction notes

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