Hydrochloric Acid → HCID 68520062, compound

HRID 1948331Notes

Reaction equation

HRID 1948331 reaction equation
[C:1]([C:3]1([NH:6][C:7]([C:9]2[N:10]=[C:11]([N:19]3[CH2:24][CH2:23][C@@H:22]([NH:25][C:26]([C:28]4[NH:29][C:30]([CH3:35])=[C:31]([Cl:34])[C:32]=4[Cl:33])=[O:27])[C@@H:21]([O:36][CH3:37])[CH2:20]3)[S:12][C:13]=2[C:14]([O:16]CC)=[O:15])=[O:8])[CH2:5][CH2:4]1)#[N:2].C(=O)([O-])[O-].[K+].[K+].Cl>CO.O>[C:1]([C:3]1([NH:6][C:7]([C:9]2[N:10]=[C:11]([N:19]3[CH2:24][CH2:23][C@@H:22]([NH:25][C:26]([C:28]4[NH:29][C:30]([CH3:35])=[C:31]([Cl:34])[C:32]=4[Cl:33])=[O:27])[C@@H:21]([O:36][CH3:37])[CH2:20]3)[S:12][C:13]=2[C:14]([OH:16])=[O:15])=[O:8])[CH2:5][CH2:4]1)#[N:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 59406919HCID 59406919, compound

Product 1

HCID 68520062HCID 68520062, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

To a solution of ethyl 4-{[(1-cyanocyclopropyl)amino]carbonyl}-2-((3S,4R)-4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}-3-methoxypiperidin-1-yl)-1,3-thiazole-5-carboxylate (0.09 g, 0.16 mmol, Example 230) in methanol (2 mL) was added potassium carbonate (0.022 g, 0.16 mmol) and water (0.5 mL). After heating in the microwave for 30 min at 80°, reaction was complete by LCMS analysis. The reaction mixture was diluted with water and acidified with 1N HCl. After concentrating to remove methanol, the resulting white precipitate was filtered, washed with water and dried (0.071 g). MS (ES) M+H+: 541 for C21H22Cl2N6O5S; NMR: 1.33-1.41 (m, 2 H) 1.64 (s, 2 H) 1.75 (s, 2 H) 2.19 (s, 3 H) 3.37 (s, 3H) 3.43 (s, 1 H) 3.57 (s, 1 H) 4.08 (s, 1 H) 4.27 (d, 2 H) 4.40 (s, 1 H) 7.16 (d, 1 H) 9.87 (s, 1 H) 12.17 (s, 1 H).

Workup

  1. temperatureAfter heating in the microwave for 30 min at 80°
  2. customreaction
  3. concentrationAfter concentrating
  4. customto remove methanol
  5. filtrationthe resulting white precipitate was filtered
  6. washwashed with water
  7. customdried (0.071 g)

Sources & evidence

ORD record
ord-4032e0ba2b8d41c8b1107d3691355f57
Source dataset
uspto-grants-2013_03
Patent number
US08399489B2

Reaction notes

Loading…