Thiomorpholine 1,1-dioxide → HCID 178457846, compound

HRID 518748Notes

Reaction equation

HRID 518748 reaction equation
Cl[C:2]1[CH:7]=[C:6]([NH:8][C@@H:9]2[CH2:14][CH2:13][C@H:12]([C:15]([NH:17][CH:18]([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]2)[C:5]([N+:21]([O-:23])=[O:22])=[CH:4][N:3]=1.[NH:24]1[CH2:29][CH2:28][S:27](=[O:31])(=[O:30])[CH2:26][CH2:25]1>CC(O)C>[CH:18]([NH:17][C:15]([C@H:12]1[CH2:13][CH2:14][C@@H:9]([NH:8][C:6]2[C:5]([N+:21]([O-:23])=[O:22])=[CH:4][N:3]=[C:2]([N:24]3[CH2:29][CH2:28][S:27](=[O:31])(=[O:30])[CH2:26][CH2:25]3)[CH:7]=2)[CH2:10][CH2:11]1)=[O:16])([CH3:20])[CH3:19]

Participants

4

Reactant 2

HCID 6484228Thiomorpholine 1,1-dioxideHCID 178457831HCID 178457831, compound

Product 1

HCID 178457846HCID 178457846, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A suspension of cis-4-(2-chloro-5-nitropyridin-4-ylamino)-N-isopropylcyclohexanecarboxamide (100 mg, 0.293 mmol) and thiomorpholine-1,1-dioxide (198 mg, 1.467 mmol) in 2-propanol (1 mL) was irradiated in the microwave for 90 minutes at 170° C. The reaction mixture was concentrated, adsorbed onto a plug of silica gel, and purified by column chromatography, eluting with 0-100% EtOAc in DCM, to provide cis-N-isopropyl-4-(5-nitro-2-(1,1-dioxido-4-thiomorpholinyl)pyridin-4-ylamino)cyclohexanecarboxamide as a yellow powder (112 mg, 87% yield). MS, m/z (C19H29N5O5S): Calcd, 439.2. found, 440.1 [M+H].

Workup

  1. customwas irradiated in the microwave for 90 minutes at 170° C
  2. concentrationThe reaction mixture was concentrated
  3. custompurified by column chromatography
  4. washeluting with 0-100% EtOAc in DCM

Sources & evidence

ORD record
ord-bed8a5e1656540aab49802a765ccd3b2
Source dataset
uspto-grants-2015_08
Patent number
US09115127B2

Reaction notes

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