Methyl chloroformate → HCID 131730325, compound

HRID 1948318Notes

Reaction equation

HRID 1948318 reaction equation
[NH2:1][C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][C:5]([N:13]2[CH2:18][CH2:17][C@H:16]([NH:19][C:20]([C:22]3[NH:23][C:24]([CH3:29])=[C:25]([Cl:28])[C:26]=3[Cl:27])=[O:21])[C@H:15]([O:30][CH3:31])[CH2:14]2)=[N:4][CH:3]=1.[CH3:32][O:33][C:34](Cl)=[O:35]>N1C=CC=CC=1>[Cl:27][C:26]1[C:25]([Cl:28])=[C:24]([CH3:29])[NH:23][C:22]=1[C:20]([NH:19][C@H:16]1[CH2:17][CH2:18][N:13]([C:5]2[CH:6]=[C:7]([C:2]([NH:1][C:34]([O:33][CH3:32])=[O:35])=[CH:3][N:4]=2)[C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:14][C@H:15]1[O:30][CH3:31])=[O:21]

Participants

4

Reactant 2

HCID 6586Methyl chloroformateHCID 131730323HCID 131730323, compound

Product 1

HCID 131730325HCID 131730325, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Methylchlorofomate (15 μl, 0.19 mmol) was added to a solution of 60 mg (0.13 mmol) of Cis(±)-ethyl 5-amino-2-(4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}-3-methoxypiperidin-1-yl)isonicotinate (Example 194) in 3 ml pyridine. After stirring at room temperature overnight, 7 μl more methylchloroformate was added. Solvent was removed and the residue was partitioned between EtOAc and NaHCO3 (aqueous). The EtOAc was separated and washed with water and brine. Drying (MgSO4) and removal of solvent gave 43 mg of product. NMR (d6-DMSO): 1.3 (t, 3H), 1.7 (m, 2H) 2.2 (s, 3H), 3.1 (m, 2H), 3.3 (s, 3H), 3.5 (m, 1H), 3.6 (s, 3H), 4.0-4.3 (m, 4H), 4.6 (m, 1H), 7.05 (m, 1H), 7.15 (m, 1H), 8.2 (s, 1H), 9.1 (s, 1H), 12.2 (s, 1H).

Workup

  1. customSolvent was removed
  2. customthe residue was partitioned between EtOAc and NaHCO3 (aqueous)
  3. customThe EtOAc was separated
  4. washwashed with water and brine
  5. customDrying
  6. custom(MgSO4) and removal of solvent

Sources & evidence

ORD record
ord-40c64f3cd1fa46e297496f6952c07e3e
Source dataset
uspto-grants-2013_03
Patent number
US08399489B2

Reaction notes

Loading…