Water → HCID 59380227, compound

HRID 2353718Notes

Reaction equation

HRID 2353718 reaction equation
Cl[C:2]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:3].[NH2:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[N:23]=[C:22]([CH2:24][S:25]([CH2:28][CH2:29][OH:30])(=[O:27])=[O:26])[CH:21]=[C:20]([N:31]3[CH2:36][CH2:35][O:34][CH2:33][C@@H:32]3[CH3:37])[N:19]=2)=[CH:14][CH:13]=1.C(=O)(O)[O-].[Na+].O>O1CCOCC1>[OH:30][CH2:29][CH2:28][S:25]([CH2:24][C:22]1[CH:21]=[C:20]([N:31]2[CH2:36][CH2:35][O:34][CH2:33][C@@H:32]2[CH3:37])[N:19]=[C:18]([C:15]2[CH:14]=[CH:13][C:12]([NH:11][C:2](=[O:3])[O:4][C:5]3[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=3)=[CH:17][CH:16]=2)[N:23]=1)(=[O:26])=[O:27]

Participants

6

Reactant 4

HCID 962WaterHCID 15891Phenyl chloroformateHCID 516892Sodium BicarbonateHCID 59379882HCID 59379882, compound

Product 1

HCID 59380227HCID 59380227, compoundYield 123.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Phenyl chloroformate (0.046 mL, 0.36 mmol) was added to 2-[[2-(4-aminophenyl)-6-[(3S)-3-methylmorpholin-4-yl]pyrimidin-4-yl]methylsulfonyl]ethanol (0.143 g, 0.36 mmol) and sodium bicarbonate (0.046 g, 0.55 mmol) in dioxane (20 mL) at RT under air. The resulting slurry was stirred at RT for 2 hours. Water was added and the mixture extracted with DCM three times. The combined organics were dried (MgSO4), filtered and concentrated in vacuo to give the desired material as a yellow solid (0.228 g).

Workup

  1. extractionthe mixture extracted with DCM three times
  2. dry with materialThe combined organics were dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-017dd7404bac4291a9efba0d2628e21f
Source dataset
uspto-grants-2010_07
Patent number
US07750003B2

Reaction notes

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