Acetyl chloride → (6S-cis)-N-[2-chloro-4-fluoro-5-(6-fluorotetrahydro-1,3-dioxo-1H-pyrrolo[1,2-c]imidazol-2(3H)-yl)phenyl]-N-[(chloromethyl)sulfonyl]acetamide

HRID 1107253Notes

Reaction equation

HRID 1107253 reaction equation
[Cl:1][CH2:2][S:3]([NH:6][C:7]1[CH:12]=[C:11]([N:13]2[C:17](=[O:18])[C@H:16]3[CH2:19][C@H:20]([F:22])[CH2:21][N:15]3[C:14]2=[O:23])[C:10]([F:24])=[CH:9][C:8]=1[Cl:25])(=[O:5])=[O:4].[C:26](Cl)(=[O:28])[CH3:27]>ClCCl.N1C=CC=CC=1>[Cl:25][C:8]1[CH:9]=[C:10]([F:24])[C:11]([N:13]2[C:17](=[O:18])[C@H:16]3[CH2:19][C@H:20]([F:22])[CH2:21][N:15]3[C:14]2=[O:23])=[CH:12][C:7]=1[N:6]([S:3]([CH2:2][Cl:1])(=[O:5])=[O:4])[C:26](=[O:28])[CH3:27]

Participants

5

Reactant 2

HCID 6367Acetyl chlorideHCID 11037075Profluazol

Product 1

HCID 21968478(6S-cis)-N-[2-chloro-4-fluoro-5-(6-fluorotetrahydro-1,3-dioxo-1H-pyrrolo[1,2-c]imidazol-2(3H)-yl)phenyl]-N-[(chloromethyl)sulfonyl]acetamide

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of the title compound of Example 1, Step H (4.14 g, 10 mmol) in anhydrous dichloromethane (200 mL) and pyridine (5 mL) was added a solution of acetyl chloride (0.863 g, 11 mmol) in dichloromethane (10 mL) dropwise at room temperature. After completion of the reaction (monitored by tlc), the organic phase was washed with water (50 mL) and diluted with HCl (5%, 50 mL). The organic layer was separated, dried (MgSO4), and the solvent was removed in vacuo to give the title compound of Step A, a compound of this invention, as a white solid (4.3 g, 94%) melting at 198-200° C. 1H NMR (CDCl3) δ 7.56 (m, 2H), 5.52 (m, 1H), 5.40 (dd, 1H), 4.84 (d, 1H), 4.62 (dd, 1H), 4.08 (m, 1H), 3.62 (m, 1H), 2.68 (m, 1H), 2.05 (s, 3H), 1.98 (m, 1H).

Workup

  1. customAfter completion of the reaction (monitored by tlc)
  2. washthe organic phase was washed with water (50 mL)
  3. additiondiluted with HCl (5%, 50 mL)
  4. customThe organic layer was separated
  5. dry with materialdried (MgSO4)
  6. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-dc0482fbf40c417ca1b53d15b9cce9c9
Source dataset
uspto-grants-2000_05
Patent number
US06060432

Reaction notes

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