Methylamine → HCID 131730321, compound

HRID 1948314Notes

Reaction equation

HRID 1948314 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C@H:11]([NH:14][C:15]([C:17]2[NH:18][C:19]([CH3:24])=[C:20]([Cl:23])[C:21]=2[Cl:22])=[O:16])[C@H:10]([CH2:25]OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:37][NH2:38]>C1COCC1.CCOC(C)=O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C@H:11]([NH:14][C:15]([C:17]2[NH:18][C:19]([CH3:24])=[C:20]([Cl:23])[C:21]=2[Cl:22])=[O:16])[C@H:10]([CH2:25][NH:38][CH3:37])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 6329MethylamineHCID 131730316HCID 131730316, compound2×

Product 1

HCID 131730321HCID 131730321, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

Cis(±)tert-butyl-4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}-3-({[(4-methylphenyl)sulfonyl]oxy}methyl)-piperidine-1-carboxylate (Intermediate 72; 500 mg, 0.89 mmol) was dissolved in 5 ml of a 2.0 M THF solution containing MeNH2. The reaction vessel was sealed and heated to 100° C. for 2 h. The mixture was cooled to room temperature and diluted with EtOAc, then washed with water. The organic layer was dried over Na2SO4, filtered and concentrated to a crude solid foam which was used without further purification. MS (ES)MH+: 419 for C18H28Cl2N4O3.

Workup

  1. customThe reaction vessel was sealed
  2. temperatureThe mixture was cooled to room temperature
  3. washwashed with water
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated to a crude solid foam which
  7. customwas used without further purification

Sources & evidence

ORD record
ord-d38e9978824144e093c12cc416560bc5
Source dataset
uspto-grants-2013_03
Patent number
US08399489B2

Reaction notes

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