1-Hydroxybenzotriazole → 2-(N-Methylcarbamoyl)-1-[(6-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridin-2-yl)carbonyl]-4-[(6-trimethylsilylethynylbenzo[b]thien-2-yl)sulfonyl]piperazine

HRID 352968Notes

Reaction equation

HRID 352968 reaction equation
[CH3:1][NH:2][C:3]([CH:5]1[NH:10][CH2:9][CH2:8][N:7]([S:11]([C:14]2[S:18][C:17]3[CH:19]=[C:20]([C:23]#[C:24][Si:25]([CH3:28])([CH3:27])[CH3:26])[CH:21]=[CH:22][C:16]=3[CH:15]=2)(=[O:13])=[O:12])[CH2:6]1)=[O:4].[CH3:29][CH:30]1[NH:35][CH2:34][C:33]2[S:36][C:37]([C:39]([O-])=[O:40])=[N:38][C:32]=2[CH2:31]1.[Li+].Cl.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1>CN(C)C=O.C(Cl)Cl>[CH3:1][NH:2][C:3]([CH:5]1[CH2:6][N:7]([S:11]([C:14]2[S:18][C:17]3[CH:19]=[C:20]([C:23]#[C:24][Si:25]([CH3:26])([CH3:28])[CH3:27])[CH:21]=[CH:22][C:16]=3[CH:15]=2)(=[O:13])=[O:12])[CH2:8][CH2:9][N:10]1[C:39]([C:37]1[S:36][C:33]2[CH2:34][NH:35][CH:30]([CH3:29])[CH2:31][C:32]=2[N:38]=1)=[O:40])=[O:4]

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 227106073-(N-methylcarbamoyl)-1-[(6-trimethylsilylethynylbenzo[b]thien-2-yl)sulfonyl]piperazineHCID 23674323Lithium 6-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine-2-carboxylate

Product 1

HCID 227104152-(N-Methylcarbamoyl)-1-[(6-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridin-2-yl)carbonyl]-4-[(6-trimethylsilylethynylbenzo[b]thien-2-yl)sulfonyl]piperazine

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

In N,N-dimethylformamide (5 ml) was dissolved 3-(N-methylcarbamoyl)-1-[(6-trimethylsilylethynylbenzo[b]thien-2-yl)sulfonyl]piperazine (218 mg), followed by the addition of lithium 6-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine-2-carboxylate (188 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (240 mg) and 1-hyroxybenzotriazole (68 mg). The resulting mixture was stirred at room temperature for 30 minutes. The reaction mixture was diluted with methylene chloride, washed with water (twice) and then with a saturated aqueous solution of sodium bicarbonate. After drying over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure. The residue was purified by chromatography on a silica gel column (methanol:methylene chloride=3:97→5:95→7:93), whereby the title compound (90 mg) was obtained. MS (FAB) m/z: 616 (M+H)+.

Workup

  1. washwashed with water (twice) and then with a saturated aqueous solution of sodium bicarbonate
  2. dry with materialAfter drying over anhydrous sodium sulfate
  3. distillationthe solvent was distilled off under reduced pressure
  4. customThe residue was purified by chromatography on a silica gel column (methanol:methylene chloride=3:97→5:95→7:93), whereby the title compound (90 mg)
  5. customwas obtained

Sources & evidence

ORD record
ord-f3da2f299e164268b07e0b240d8d9afa
Source dataset
uspto-grants-2004_06
Patent number
US06747023B1

Reaction notes

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