Diisopropylethylamine → HCID 178504878, compound

HRID 711946Notes

Reaction equation

Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][N:5]=[C:4]2[CH:11]=[CH:12][S:13][C:3]=12.OC(C(F)(F)F)=O.[CH3:21][S:22]([CH2:25][CH2:26][C@H:27]1[CH2:32][CH2:31][C@H:30]([NH2:33])[CH2:29][CH2:28]1)(=[O:24])=[O:23].C(N(CC)C(C)C)(C)C>C(O)(C)C>[CH3:21][S:22]([CH2:25][CH2:26][C@H:27]1[CH2:28][CH2:29][C@H:30]([NH:33][C:2]2[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][N:5]=[C:4]3[CH:11]=[CH:12][S:13][C:3]=23)[CH2:31][CH2:32]1)(=[O:23])=[O:24]

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 7-chloro-6-nitrothieno[3,2-b]pyridine (0.10 g, 0.46 mmol), trans-4-[2-(methylsulfonyl)ethyl]cyclohexanamine TFA salt (0.12 g, 0.60 mmol) and N,N-diisopropylethylamine (0.40 mL, 2.3 mmol) in isopropyl alcohol (1.0 mL) was heated at 90° C. for 2 h. The reaction mixture was concentrated and purified on silica gel (eluting with 0 to 45% EtOAc in dichloromethane) to give the desired product. LCMS calculated for C16H22N3O4S2 (M+H)+: m/z=384.1. Found: 384.0.

Workup

concentrationThe reaction mixture was concentrated
custompurified on silica gel (eluting with 0 to 45% EtOAc in dichloromethane)

Sources & evidence

ORD record: ord-8047f80f66234d70b3ab60c8515021d5
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181271B2

Reaction notes

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