Diisopropylethylamine → HCID 178526783, compound

HRID 711952Notes

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

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 7-chloro-6-nitrothieno[3,2-b]pyridine (0.10 g, 0.46 mmol), cis-4-(1H-1,2,4-triazol-1-yl)cyclohexanamine TFA salt (0.10 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 resulting mixture was concentrated and purified on silica gel (eluting with 0 to 10% EtOAc in dichloromethane) to give the desired product (32 mg, 20%). LCMS calculated for C15H17N6O2S (M+H)+: m/z=345.1. Found: 345.0.

Workup

concentrationThe resulting mixture was concentrated
custompurified on silica gel (eluting with 0 to 10% EtOAc in dichloromethane)

Sources & evidence

ORD record: ord-89b61701314440bf8231f8d6ea36c50f
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181271B2

Reaction notes

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