4-Methylmorpholine → HCID 70562192, compound

HRID 1427310Notes

Reaction equation

HRID 1427310 reaction equation
[CH2:1]([S:3](Cl)(=[O:5])=[O:4])[CH3:2].[NH2:7][C:8]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:9]=1[CH:10]=[CH:11][N:12]2[C:17]([C:24]1[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=1)([CH2:22][CH3:23])[C:18]([O:20][CH3:21])=[O:19].CN1CCOCC1>C(Cl)Cl>[Cl:30][C:27]1[CH:26]=[CH:25][C:24]([C:17]([N:12]2[C:13]3[C:9](=[C:8]([NH:7][S:3]([CH2:1][CH3:2])(=[O:5])=[O:4])[CH:16]=[CH:15][CH:14]=3)[CH:10]=[CH:11]2)([CH2:22][CH3:23])[C:18]([O:20][CH3:21])=[O:19])=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 11667Ethanesulfonyl chloride2×HCID 70565237HCID 70565237, compound

Product 1

HCID 70562192HCID 70562192, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethanesulfonyl chloride (0.26 g, 2 mmol) was added to a stirred solution of methyl 2-(4-amino-1H-indol-1-yl)-2-(4-chlorophenyl)butanoate (0.58 g, 1.7 mmol), as described in Example 3 Step B, and 4-methylmorpholine (0.25 g, 2.5 mmol) in DCM (8 mL) at 0° C. After 30 min, an additional portion of ethanesulfonyl chloride (0.1 g, 1 mmol) was added. After 1 h, the reaction mixture was partitioned between DCM and saturated aqueous ammonium chloride. The layers were separated and the aqueous layer was extracted with DCM. The combined organic layers were washed with brine, dried sodium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel flash chromatography (PE:EA=2:1) to afford the title compound. LC/MS m/z=435.1 [M+H]+.

Workup

  1. waitAfter 1 h
  2. customthe reaction mixture was partitioned between DCM and saturated aqueous ammonium chloride
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with DCM
  5. washThe combined organic layers were washed with brine, dried sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by silica gel flash chromatography (PE:EA=2:1)

Sources & evidence

ORD record
ord-3ead65c0c8df4bd09e165ce8fd9f97a9
Source dataset
uspto-grants-2015_01
Patent number
US08933113B2

Reaction notes

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