Diisopropylethylamine → HCID 86717463, compound

HRID 712003Notes

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.[C:14]([O:17][CH2:18][CH:19]1[CH:24]=[CH:23][C@H:22]([NH2:25])[CH2:21][O:20]1)(=[O:16])[CH3:15].C(N(CC)C(C)C)(C)C>C(O)(C)C>[C:14]([O:17][CH2:18][CH:19]1[CH:24]=[CH:23][C@H:22]([NH:25][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)[CH2:21][O:20]1)(=[O:16])[CH3:15]

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 7-chloro-6-nitrothieno[3,2-b]pyridine (156 mg, 0.727 mmol), [(5S)-5-amino-5,6-dihydro-2H-pyran-2-yl]methyl acetate (129 mg, 0.754 mmol) and N,N-diisopropylethylamine (0.26 mL, 1.5 mmol) in isopropyl alcohol (1.7 mL) was heated at 90° C. for 2 h. The reaction mixture was concentrated and purified with flash chromatography to give the desired product (0.21 g 83%). LCMS calculated for C15H16N3O5S (M+H)+: m/z=350.1. Found: 350.0.

Workup

concentrationThe reaction mixture was concentrated
custompurified with flash chromatography

Sources & evidence

ORD record: ord-eadb3348dba24821a5ca424ed60d271d
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181271B2

Reaction notes

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