Methylorthoformate → HCID 86725379, compound

HRID 1503822Notes

Reaction equation

HRID 1503822 reaction equation
[C:1]([C:4]1[C:5]([NH:14][C:15]2[C:20]([F:21])=[CH:19][C:18]([N:22]3[CH2:27][CH2:26][N:25]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:24][CH2:23]3)=[C:17]([F:35])[CH:16]=2)=[N:6][C:7]([S:12][CH3:13])=[N:8][C:9]=1[NH:10][NH2:11])(=[O:3])[NH2:2].[CH:36]([O-])([O-])OC>CC(N(C)C)=O>[C:1]([C:4]1[C:9]2[N:8]([CH:36]=[N:11][N:10]=2)[C:7]([S:12][CH3:13])=[N:6][C:5]=1[NH:14][C:15]1[C:20]([F:21])=[CH:19][C:18]([N:22]2[CH2:23][CH2:24][N:25]([C:28]([O:30][C:31]([CH3:32])([CH3:34])[CH3:33])=[O:29])[CH2:26][CH2:27]2)=[C:17]([F:35])[CH:16]=1)(=[O:3])[NH2:2]

Participants

4

Reactant 2

HCID 53629101MethylorthoformateHCID 86725377HCID 86725377, compound

Product 1

HCID 86725379HCID 86725379, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of the product of Example 15E (281 mg, 0.55 mmol) in dimethylacetamide (5 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, 9/1 petroleum 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: 521 (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-42ba2b06b9cf465ea13ef487322c6638
Source dataset
uspto-grants-2015_12
Patent number
US09212192B2

Reaction notes

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