Triethylamine → Methyl 1-{[(1,4-dichloro-7-isoquinolinyl)sulphonyl]amino}-cyclohexanecarboxylate

HRID 2289812Notes

Reaction equation

HRID 2289812 reaction equation
[NH2:1][C:2]1([C:8]([O:10][CH3:11])=[O:9])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.CCN(CC)CC.[Cl:19][C:20]1[C:29]2[C:24](=[CH:25][CH:26]=[C:27]([S:30](Cl)(=[O:32])=[O:31])[CH:28]=2)[C:23]([Cl:34])=[CH:22][N:21]=1>C(Cl)Cl>[Cl:19][C:20]1[C:29]2[C:24](=[CH:25][CH:26]=[C:27]([S:30]([NH:1][C:2]3([C:8]([O:10][CH3:11])=[O:9])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]3)(=[O:32])=[O:31])[CH:28]=2)[C:23]([Cl:34])=[CH:22][N:21]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 4048819Methyl 1-aminocyclohexanoateHCID 166582941,4-Dichloroisoquinoline-7-sulfonyl chloride

Product 1

HCID 16658027Methyl 1-{[(1,4-dichloro-7-isoquinolinyl)sulphonyl]amino}-cyclohexanecarboxylateYield 22.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
23 °C

Procedure

A mixture of methyl 1-aminocyclohexanecarboxylate (325 mg, 1.68 mmol), NEt3 (0.49 mL, 3.5 mmol) and 1,4-dichloro-7-isoquinolinesulphonyl chloride (415 mg, 1.40 mmol) in CH2Cl2 (30 mL) was stirred at 23° C. for 16 h. The mixture was diluted with CH2Cl2, washed with dilute HCl (2 M), saturated aqueous NaHCO3, brine, dried (Na2SO4) and evaporated in vacuo. The residue was purified by column chromatography upon silica gel using hexane-EtOAc (80:20 to 70:30) as eluant, followed by trituration with i-Pr2O, to give to give methyl 1-{[(1,4-dichloro-7-isoquinolinyl)sulphonyl]amino}-cyclohexanecarboxylate (132 mg, 0.32 mmol) as a white solid.

Workup

  1. washwashed with dilute HCl (2 M), saturated aqueous NaHCO3, brine
  2. dry with materialdried (Na2SO4)
  3. customevaporated in vacuo
  4. customThe residue was purified by column chromatography upon silica gel
  5. customto give

Sources & evidence

ORD record
ord-e996a60fd7694cab959b77ab7542a524
Source dataset
uspto-grants-2000_07
Patent number
US06093731

Reaction notes

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