2-Chloro-1,1,1-triethoxyethane → 1-[(2S)-Bicyclo[2.2.1]hept-2-yl]-2-(chloromethyl)-1H-imidazo[4,5-d]thieno[3,2-b]pyridine

HRID 712010Notes

Reaction equation

[CH:1]12[CH2:7][CH:4]([CH2:5][CH2:6]1)[CH2:3][C@@H:2]2[NH:8][C:9]1[C:14]([NH2:15])=[CH:13][N:12]=[C:11]2[CH:16]=[CH:17][S:18][C:10]=12.[Cl:19][CH2:20][C:21](OCC)(OCC)OCC>C(O)(=O)C>[CH:1]12[CH2:7][CH:4]([CH2:5][CH2:6]1)[CH2:3][C@@H:2]2[N:8]1[C:9]2=[C:10]3[S:18][CH:17]=[CH:16][C:11]3=[N:12][CH:13]=[C:14]2[N:15]=[C:21]1[CH2:20][Cl:19]

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of N7-[(2S)-bicyclo[2.2.1]hept-2-yl]thieno[3,2-b]pyridine-6,7-diamine (0.060 g, 0.23 mmol) and 2-chloro-1,1,1-triethoxyethane (0.134 mL, 0.700 mmol) in acetic acid (0.2 mL) was stirred at 120° C. for 30 min. The solvent was removed and the resultant residue was dissolved in dichloromethane and purified on silica gel (eluting with 0-5% MeOH in dichloromethane) to give the desired product. LCMS calculated for C16H17ClN3S (M+H)+: m/z=318.1. Found: 318.0.

Workup

customThe solvent was removed
dissolutionthe resultant residue was dissolved in dichloromethane
custompurified on silica gel (eluting with 0-5% MeOH in dichloromethane)

Sources & evidence

ORD record: ord-aa9381768a3f410daa003bbfd89acadf
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181271B2

Reaction notes

Loading…