Methylamine → HCID 58869176, compound

HRID 2355207Notes

Reaction equation

HRID 2355207 reaction equation
[C:1]1([S:7]([C:10]2[C:19]([C:20](O)=[O:21])=[C:18]3[C:13]([CH2:14][CH2:15][CH:16]([CH2:23][N:24]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH3:25])[O:17]3)=[CH:12][CH:11]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O=S(Cl)Cl.[CH3:37][NH2:38]>C(Cl)Cl.C(#N)C>[C:29]([O:28][C:26](=[O:27])[N:24]([CH2:23][CH:16]1[CH2:15][CH2:14][C:13]2[C:18](=[C:19]([C:20](=[O:21])[NH:38][CH3:37])[C:10]([S:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)(=[O:8])=[O:9])=[CH:11][CH:12]=2)[O:17]1)[CH3:25])([CH3:31])([CH3:30])[CH3:32]

Participants

6

Reactant 3

HCID 6329MethylamineHCID 24386Thionyl ChlorideHCID 58869174HCID 58869174, compound

Product 1

HCID 58869176HCID 58869176, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 7-benzenesulfonyl-2-[(tert-butoxycarbonyl-methyl-amino)-methyl]-chroman-8-carboxylic acid (52 mg, 0.113 mmol) in DCM (10 mL) was added SOCl2 (25 μL, 0.339 mmol). The reaction was heated to reflux for 2 hours, then a solution of MeNH2 (40% in water, 0.5 mL) in acetonitrile (5 mL) was added and the mixture was allowed to stir for 1 hour. The reaction was concentrated in vacuo and the residue was purified via flash chromatography (DCM/MeOH, 98/2) to give (7-benzenesulfonyl-8-methylcarbamoyl-chroman-2-ylmethyl)-methyl-carbamic acid tert-butyl ester (52 mg, 98% yield) as clear oil.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 2 hours
  3. concentrationThe reaction was concentrated in vacuo
  4. customthe residue was purified via flash chromatography (DCM/MeOH, 98/2)

Sources & evidence

ORD record
ord-9fa6e894dfea4d0192af5d6d58b5ddae
Source dataset
uspto-grants-2010_07
Patent number
US07754759B2

Reaction notes

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