Triethylamine → 1-(5-acetyl-4-methyl-thiazol-2-yl)-3-{(3R,4S)-4-[(S)-3-(4-fluorobenzyl)-piperidine-1-carbonyl]-1,1-dioxo-tetrahydro-1lambda6-thiophen-3-yl}-urea

HRID 497502Notes

Reaction equation

HRID 497502 reaction equation
[NH2:1][C@@H:2]1[CH2:6][S:5](=[O:8])(=[O:7])[CH2:4][C@H:3]1[C:9]([N:11]1[CH2:16][CH2:15][CH2:14][C@@H:13]([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)[CH2:12]1)=[O:10].C1([O:31][C:32](=O)[NH:33][C:34]2[S:35][C:36]([C:40](=[O:42])[CH3:41])=[C:37]([CH3:39])[N:38]=2)C=CC=CC=1.C(N(CC)CC)C>CN(C)C=O>[C:40]([C:36]1[S:35][C:34]([NH:33][C:32]([NH:1][C@@H:2]2[C@@H:3]([C:9]([N:11]3[CH2:16][CH2:15][CH2:14][C@@H:13]([CH2:17][C:18]4[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=4)[CH2:12]3)=[O:10])[CH2:4][S:5](=[O:7])(=[O:8])[CH2:6]2)=[O:31])=[N:38][C:37]=1[CH3:39])(=[O:42])[CH3:41]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 22259036Phenyl (5-acetyl-4-methyl-1,3-thiazol-2-yl)carbamateHCID 69748830[(3R,4S)-4-Amino-1,1-dioxo-tetrahydrothiophen-3-yl]-[(S)-3-(4-fluorobenzyl)-piperidin-1-yl]-methanone

Product 1

HCID 213624291-(5-acetyl-4-methyl-thiazol-2-yl)-3-{(3R,4S)-4-[(S)-3-(4-fluorobenzyl)-piperidine-1-carbonyl]-1,1-dioxo-tetrahydro-1lambda6-thiophen-3-yl}-ureaYield 55%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

[(3R,4S)-4-Amino-1,1-dioxo-tetrahydrothiophen-3-yl]-[(S)-3-(4-fluorobenzyl)-piperidin-1-yl]-methanone (50 mg, 141 μmol) and [5-acetyl-4-methylthiazol-2-yl]-carbamic acid phenyl ester (43 mg, 155 μmol) were dissolved in N,N-dimethylformamide (1 mL) and treated with triethylamine (22 μL, 155 μmol). The mixture was stirred at room temperature for 94 h, and then concentrated. The residue was purified by flash column chromatography (4% methanol/dichloromethane containing 0.4% aqueous ammonium hydroxide) to provide a white solid (41 mg, 55%).

Workup

  1. concentrationconcentrated
  2. customThe residue was purified by flash column chromatography (4% methanol/dichloromethane containing 0.4% aqueous ammonium hydroxide)

Sources & evidence

ORD record
ord-39d033038a4b4cabac805ce08d21e518
Source dataset
uspto-grants-2005_09
Patent number
US06949546B2

Reaction notes

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