Triethylamine → HCID 178472459, compound

HRID 2289815Notes

Reaction equation

HRID 2289815 reaction equation
[NH2:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:4][CH2:3]1.CCN(CC)CC.[Cl:20][C:21]1[C:30]2[C:25](=[CH:26][CH:27]=[C:28]([S:31](Cl)(=[O:33])=[O:32])[CH:29]=2)[C:24]([Cl:35])=[CH:23][N:22]=1>C(Cl)Cl>[Cl:20][C:21]1[C:30]2[C:25](=[CH:26][CH:27]=[C:28]([S:31]([NH:1][C@H:2]3[CH2:3][CH2:4][C@H:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:6][CH2:7]3)(=[O:33])=[O:32])[CH:29]=2)[C:24]([Cl:35])=[CH:23][N:22]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 166582941,4-Dichloroisoquinoline-7-sulfonyl chlorideHCID 178472434HCID 178472434, compound

Product 1

HCID 178472459HCID 178472459, compoundYield 80.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A mixture of ethyl trans-4-aminocyclohexanecarboxylate (168 mg, 0.81 mmol), NEt3 (0.22 mL, 1.6 mmol) and 1,4-dichloro-7-isoquinolinesulphonyl chloride (200 mg, 0.67 mmol) in CH2Cl2 (8 mL) was stirred at 0° C. for 1 h. The mixture was diluted with CH2Cl2 (100 mL), was washed with dilute HCl (50 mL, 1 M), water, dried (MgSO4) and evaporated in vacuo to give ethyl trans-4-{[(1,4-dichloro-7-isoquinolinyl)sulphonyl]amino}cyclohexanecarboxylate (232 mg, 0.54 mmol) as a white solid.

Workup

  1. washwas washed with dilute HCl (50 mL, 1 M), water
  2. dry with materialdried (MgSO4)
  3. customevaporated in vacuo

Sources & evidence

ORD record
ord-5b62c766aa43492b8dc8463f822dad2e
Source dataset
uspto-grants-2000_07
Patent number
US06093731

Reaction notes

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