Diisopropylethylamine → ethyl (1R,3S)-3-[(6-nitrothieno[3,2-b]pyridin-7-yl)amino]cyclopentanecarboxylate

HRID 712080Notes

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.FC(F)(F)C(O)=O.[NH2:21][C@H:22]1[CH2:26][CH2:25][C@@H:24]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH2:23]1.C(N(CC)C(C)C)(C)C>C(O)(C)C>[N+:8]([C:7]1[C:2]([NH:21][C@H:22]2[CH2:26][CH2:25][C@@H:24]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH2:23]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

To a stirred mixture of 7-chloro-6-nitrothieno[3,2-b]pyridine (0.18 g, 0.84 mmol) and ethyl (1R,3S)-3-aminocyclopentanecarboxylate trifluoroacetate (0.25 g, 0.92 mmol) in isopropyl alcohol (2.3 mL) was added N,N-diisopropylethylamine (0.73 mL, 4.2 mmol). The resulting mixture was stirred at 90° C. for 100 min, and then the solvent was evaporated. The crude residue was purified on silica gel, eluted with 10-60% EtOAc in hexanes to give 0.15 g (55%) of the desired product. LCMS calculated for C15H18N3O4S (M+H)+: m/z=336.1. Found: 336.0.

Workup

customthe solvent was evaporated
customThe crude residue was purified on silica gel
washeluted with 10-60% EtOAc in hexanes

Sources & evidence

ORD record: ord-9122a6cf0ac44fff9e43ba404a11b12f
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181271B2

Reaction notes

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