4-Methylmorpholine → HCID 16221917, compound

HRID 1678479Notes

Reaction equation

HRID 1678479 reaction equation
[O:1]=[S:2]1(=[O:36])[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16]([C:18]3[CH:23]=[CH:22][C:21]([C:24]4[CH:29]=[C:28]([NH2:30])[CH:27]=[CH:26][C:25]=4[O:31][C:32]([F:35])([F:34])[F:33])=[CH:20][CH:19]=3)=[O:17])=[CH:11][CH:10]=2)[CH2:4][CH2:3]1.CN1CCOCC1.[CH:44]1([C:47](Cl)=[O:48])[CH2:46][CH2:45]1>ClCCl>[O:36]=[S:2]1(=[O:1])[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:10]=[CH:11][C:12]([NH:15][C:16]([C:18]3[CH:23]=[CH:22][C:21]([C:24]4[CH:29]=[C:28]([NH:30][C:47]([CH:44]5[CH2:46][CH2:45]5)=[O:48])[CH:27]=[CH:26][C:25]=4[O:31][C:32]([F:35])([F:33])[F:34])=[CH:20][CH:19]=3)=[O:17])=[CH:13][CH:14]=2)[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 77637Cyclopropanecarbonyl chlorideHCID 59822389HCID 59822389, compound

Product 1

HCID 16221917HCID 16221917, compoundYield 90.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5′-Amino-2′-trifluoromethoxy-biphenyl-4-carboxylic acid [4-(1,1-dioxo-1lambda*6*-thiomorpholin-4-ylmethyl)-phenyl]-amide (50 mg) in dichloromethane (1 ml) containing N-methylmorpholine (0.03 ml) was treated with cyclopropanecarbonyl chloride (9 mg), the mixture being stirred for 18 h. The solvent was then evaporated and the residue purified on silica gel. Elution with dichloromethane:ethanol:0.880 ammonia; 800:8:1 to 100:8:1 gave a colourless solid (46 mg).

Workup

  1. customThe solvent was then evaporated
  2. customthe residue purified on silica gel
  3. washElution with dichloromethane

Sources & evidence

ORD record
ord-d198653532694c78bc630a63ca28a3eb
Source dataset
uspto-grants-2011_08
Patent number
US08008303B2

Reaction notes

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