Ethanol → HCID 9823239, compound

HRID 1057745Notes

Reaction equation

HRID 1057745 reaction equation
CCO.C([Cl:7])(=O)C.[CH3:8][C:9]([C:12]1[O:16][C:15]([CH2:17][S:18][C:19]2[S:23][C:22]([NH:24][C:25]([CH:27]3[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]3)=[O:26])=[N:21][CH:20]=2)=[N:14][CH:13]=1)([CH3:11])[CH3:10]>O>[ClH:7].[CH3:11][C:9]([C:12]1[O:16][C:15]([CH2:17][S:18][C:19]2[S:23][C:22]([NH:24][C:25]([CH:27]3[CH2:28][CH2:29][NH:30][CH2:31][CH2:32]3)=[O:26])=[N:21][CH:20]=2)=[N:14][CH:13]=1)([CH3:8])[CH3:10]

Participants

5

Reactant 3

HCID 702EthanolHCID 6367Acetyl chlorideHCID 3025986BMS 387032

Product 1

HCID 9823239HCID 9823239, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 40 mL of absolute EtOH cooled in an ice-bath was added acetyl chloride (0.28 mL, 3.9 mmol) dropwise. The reaction mixture was allowed to warm to room temperature over 30 min then N-[5-[[[5-(1,1-dimethylethyl)-2-oxazolyl]methyl]-thio]-2-thiazolyl]-4-piperidinecarboxamide (1.50 g, 3.94 mmol, 1 eq) was introduced in one portion with stirring to give a thick slurry. Water (˜4 mL) was added until homogeneous then concentrated in vacuo to give a crude pale yellow solid. The crude material was recrystallized (aq EtOH) to afford the title compound (70%) as a white solid, mp 256-258°. Analysis calc'd for C17H24N4O2S2.HCl: C, 48.96; H, 6.04; N, 13.43; S, 15.38; Cl, 8.50. Found: C, 48.69; H, 5.99; N, 13.24; S, 15.27; Cl, 8.31.

Workup

  1. customto give a thick slurry
  2. concentrationthen concentrated in vacuo
  3. customto give a crude pale yellow solid
  4. customThe crude material was recrystallized (aq EtOH)

Sources & evidence

ORD record
ord-4263faddc8e148c3bdbbf0b8bfdcb0cb
Source dataset
uspto-grants-2003_02
Patent number
US06515004B1

Reaction notes

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