Hydrochloric Acid → HCID 89621241, compound

HRID 868893Notes

Reaction equation

HRID 868893 reaction equation
CO.C([Cl:6])(=O)C.Cl.[CH3:8][C:9]1([CH3:30])[O:22][C:13]2=[N:14][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:16][CH:17]=[C:12]2[C@H:11]([NH:23]S(C(C)(C)C)=O)[CH2:10]1>C(OC)(C)(C)C>[Cl-:6].[CH3:8][C:9]1([CH3:30])[O:22][C:13]2=[N:14][C:15]([C:18]([F:21])([F:19])[F:20])=[CH:16][CH:17]=[C:12]2[C@H:11]([NH3+:23])[CH2:10]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 6367Acetyl chlorideHCID 89646971HCID 89646971, compound

Product 1

HCID 89621241HCID 89621241, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Procedure

To a 0° C. solution of methanol (2.22 mL, 55 mmol) was added acetyl chloride (0.868 mL, 12.21 mmol) dropwise. This methanolic HCl solution was added to a room temperature mixture of Example 62C (2.14 g, 6.11 mmol) in methyl tert-butyl ether (20 mL). After 2 hours the solid was collected by filtration (200 mL MTBE wash) and dried at 60° C. overnight in a vacuum oven to provide the title compound (2.14 g, 6.11 mmol). 1H NMR (300 MHz, DMSO-d6) δ 8.97 (bs, 2H), 8.43 (d, J=7.8 Hz, 1H), 7.62 (d, J=7.7 Hz, 1H), 4.75-4.66 (m, 1H), 2.51-2.36 (m, 2H), 1.50 (s, 3H), 1.30 (s, 3H). MS (ESI+) m/z 247 (M+H)+.

Workup

  1. filtrationAfter 2 hours the solid was collected by filtration (200 mL MTBE wash)
  2. customdried at 60° C. overnight in a vacuum oven

Sources & evidence

ORD record
ord-6358ab71bbbd4ab2a10469646b0f4b41
Source dataset
uspto-grants-2015_03
Patent number
US08969325B2

Reaction notes

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