2-Thiophenecarbonyl chloride → HCID 74344140, compound

HRID 2421060Notes

Reaction equation

HRID 2421060 reaction equation
[N:1]1([CH:17]2[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]2)[CH2:6][CH2:5][CH:4]([N:7]2[CH:11]3[CH2:12][CH2:13][CH2:14][CH2:15][CH:10]3[NH:9][C:8]2=[O:16])[CH2:3][CH2:2]1.C(N(C(C)C)CC)(C)C.[S:32]1[CH:36]=[CH:35][CH:34]=[C:33]1[C:37](Cl)=[O:38]>ClCCl.C(Cl)(Cl)Cl>[S:32]1[CH:36]=[CH:35][CH:34]=[C:33]1[C:37]([N:20]1[CH2:21][CH2:22][CH:17]([N:1]2[CH2:2][CH2:3][CH:4]([N:7]3[CH:11]4[CH2:12][CH2:13][CH2:14][CH2:15][CH:10]4[NH:9][C:8]3=[O:16])[CH2:5][CH2:6]2)[CH2:18][CH2:19]1)=[O:38]

Participants

6

Reactant 3

HCID 789282-Thiophenecarbonyl chlorideHCID 81531DiisopropylethylamineHCID 690376871-(1,4'-bipiperidin-4-yl)octahydro-2H-benzimidazol-2-one

Product 1

HCID 74344140HCID 74344140, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of (trans (+/−))-1-(1,4′-bipiperidin-4-yl)octahydro-2H-benzimidazol-2-one. 2TFA (180 mg, 0.31 mmol) in a mixture of dichloromethane and chloroform (1:4) was added diisopropylethylamine (0.2 mL, 1.1 mmol) followed by thiophene-2-carbonyl chloride (0.1 mL, 0.6 mmol) at room temperature. The mixture stirred 48 hours and then quenched with water. Diluted in dichloromethane (60 mL) and washed with 1N NaOH (5 mL) and brine (5 mL) and concentrated in vacuo. The crude was purified by high pH prep LCMS (acetonitrile/water) to provide 26 mg of the title compound as a white solid. 1H NMR (400 MHz, CHLOROFORM-D): δ ppm 1.26-1.58 (m, 6H), 1.59-2.03 (m, 9H), 2.12-2.34 (m, 3H), 2.44-2.64 (m, 1H), 2.82-3.06 (m, 6H), 3.62-3.84 (m, 1H), 4.29-4.57 (m, 2H), 4.63 (s, 1H), 7.01 (d, J=5.08 Hz, 1H), 7.18-7.27 (m, 1H), 7.35-7.46 (m, 1H). MS (M+1): 417.3

Workup

  1. customquenched with water
  2. additionDiluted in dichloromethane (60 mL)
  3. washwashed with 1N NaOH (5 mL) and brine (5 mL)
  4. concentrationconcentrated in vacuo
  5. customThe crude was purified by high pH prep LCMS (acetonitrile/water)

Sources & evidence

ORD record
ord-52ebdd25c6c941f59e11edfceeab0144
Source dataset
uspto-grants-2011_06
Patent number
US07956069B2

Reaction notes

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