Triethylamine → HCID 178451165, compound

HRID 2289814Notes

Reaction equation

[NH2:1][C@@H:2]1[CH2:7][CH2:6][C@H:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.CCN(CC)CC.[Cl:22][C:23]1[C:32]2[C:27](=[CH:28][CH:29]=[C:30]([S:33](Cl)(=[O:35])=[O:34])[CH:31]=2)[C:26]([Cl:37])=[CH:25][N:24]=1>C(Cl)Cl>[Cl:22][C:23]1[C:32]2[C:27](=[CH:28][CH:29]=[C:30]([S:33]([NH:1][C@@H:2]3[CH2:3][CH2:4][C@H:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:6][CH2:7]3)(=[O:35])=[O:34])[CH:31]=2)[C:26]([Cl:37])=[CH:25][N:24]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A mixture of t-butyl cis-4-aminocyclohexanecarboxylate (282 mg, 1.20 mmol), NEt3 (0.33 mL, 2.37 mmol) and 1,4-dichloro-7-isoquinolinesulphonyl chloride (296 mg, 1.00 mmol) in CH2Cl2 (10 mL) was stirred at 0° C. for 1 h. The mixture was diluted with CH2Cl2 (150 mL), was washed with dilute HCl (30 mL, 1 M), water, dried (MgSO4) and evaporated in vacuo. The residue was purified by column chromatography upon silica gel using pentane-EtOAc (100:0 to 75:25) to give t-butyl cis-4-{[(1,4-dichloro-7-isoquinolinyl)sulphonyl]amino}cyclohexanecarboxylate (360 mg, 0.78 mmol) as a white solid.

Workup

washwas washed with dilute HCl (30 mL, 1 M), water
dry with materialdried (MgSO4)
customevaporated in vacuo
customThe residue was purified by column chromatography upon silica gel

Sources & evidence

ORD record: ord-7153ff796b3d4b968bb57b2895e9bb4d
Source dataset: uspto-grants-2000_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06093731

Reaction notes

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