Ammonia → HCID 86725374, compound

HRID 1503817Notes

Reaction equation

HRID 1503817 reaction equation
[C:1]([C:4]1[C:5](Cl)=[N:6][C:7]([S:33][CH3:34])=[CH:8][C:9]=1[NH:10][C:11]1[CH:16]=[CH:15][C:14]([N:17]2[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:18]2)=[CH:13][C:12]=1[S:30]([CH3:32])=[O:31])(=[O:3])[NH2:2].[NH3:36]>O1CCOCC1>[NH2:36][C:5]1[C:4]([C:1](=[O:3])[NH2:2])=[C:9]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([N:17]3[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:28])([CH3:27])[CH3:29])=[O:24])[CH2:19][CH2:18]3)=[CH:13][C:12]=2[S:30]([CH3:32])=[O:31])[CH:8]=[C:7]([S:33][CH3:34])[N:6]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 86725375HCID 86725375, compound

Product 1

HCID 86725374HCID 86725374, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of the product of Example 14E (637 mg, 1.18 mmol) and 25% aqueous ammonia (2 mL) in 1,4-dioxane (3 mL) was heated in a seated tube at 80° C. for 24 hours. After cooling to ambient temperature, the mixture was concentrated, diluted with ethyl acetate, washed with water, dried over sodium sulfate, filtered and concentrated. The residue was purified by flash chromatography on silica gel eluting with 25/1 dichloromethane/methanol to give the title compound. MS: 521 (M+H+).

Workup

  1. temperatureAfter cooling to ambient temperature
  2. concentrationthe mixture was concentrated
  3. additiondiluted with ethyl acetate
  4. washwashed with water
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by flash chromatography on silica gel eluting with 25/1 dichloromethane/methanol

Sources & evidence

ORD record
ord-c3020ef990a84360a6f45c2d730fa0d2
Source dataset
uspto-grants-2015_12
Patent number
US09212192B2

Reaction notes

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