Ammonia → HCID 86606774, compound

HRID 1352393Notes

Reaction equation

HRID 1352393 reaction equation
CO[CH:3](OC)[N:4]([CH3:6])[CH3:5].[C:9]([O:13][C:14]([N:16]1[CH2:21][CH2:20][N:19]([C:22](=[S:24])[NH2:23])[CH2:18][CH2:17]1)=[O:15])([CH3:12])([CH3:11])[CH3:10].N1(C(OC(C)(C)C)=O)CCNCC1.C(N1C=CN=C1)(N1C=CN=C1)=S.N>>[C:9]([O:13][C:14]([N:16]1[CH2:17][CH2:18][N:19]([C:22](=[S:24])[N:23]=[CH:3][N:4]([CH3:6])[CH3:5])[CH2:20][CH2:21]1)=[O:15])([CH3:12])([CH3:10])[CH3:11]

Participants

6

Reactant 5

HCID 222AmmoniaHCID 78373Dimethylformamide dimethyl acetalHCID 802641,1'-ThiocarbonyldiimidazoleHCID 143452tert-Butyl piperazine-1-carboxylateHCID 12093220tert-Butyl 4-carbamothioylpiperazine-1-carboxylate

Product 1

HCID 86606774HCID 86606774, compoundYield 95%

Conditions

Temperature
110 °C

Procedure

A mixture of 122 mmol N,N-dimethylformamide dimethyl acetal and 6.11 mmol 4-thiocarbamoyl-piperazine-1-carboxylic acid tert-butyl ester (prepared from tert-butyl 1-piperazinecarboxylate, 1,1′-thiocarbonyldiimidazole and ammonia according to the procedure of J. Med. Chem. 1998, 41, 5037–5054) was heated at 110° C. for 3 h. The reaction mixture was then concentrated in vacuo and the residue was resuspended in ethyl acetate/tetrahydrofuran (1:1) and washed with brine. The organic phase was dried over sodium sulphate and concentrated in vacuo to afford the title compound as a light yellow crystalline solid (yield 95%). MS (m/e): 301.4 (M+H+, 100%).

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo
  2. washwashed with brine
  3. dry with materialThe organic phase was dried over sodium sulphate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3981d871b0a446f2a4d2629b8a6072f5
Source dataset
uspto-grants-2007_05
Patent number
US07220744B2

Reaction notes

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