Diisopropylethylamine → 2-Chloromethyl-N-(4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-isonicotinamide

HRID 1167777Notes

Reaction equation

[CH3:1][O:2][C:3]1[C:8]2[N:9]=[C:10]([NH2:12])[S:11][C:7]=2[C:6]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)=[CH:5][CH:4]=1.C(N(C(C)C)C(C)C)C.[Cl:28][CH2:29][C:30]1[CH:31]=[C:32]([CH:36]=[CH:37][N:38]=1)[C:33](Cl)=[O:34]>O1CCCC1>[Cl:28][CH2:29][C:30]1[CH:31]=[C:32]([CH:36]=[CH:37][N:38]=1)[C:33]([NH:12][C:10]1[S:11][C:7]2[C:6]([N:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[C:8]=2[N:9]=1)=[O:34]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl-amine (2.3 g, 8.7 mmol) in tetrahydrofurane (80 ml) is added N-ethyldiisopropylamine (6.0 ml, 35 mmol) and the solution cooled to 0° C. 2-chloromethyl-isonicotinoyl chloride (2.4 g, 10.5 mmol), dissolved in tetrahydrofurane (50 ml), is added over 15 minutes and the mixture heated to 70° C. for 1 h. After evaporation of the volatile components, the residue was disolved in ethyl acetate and water, filtered and the residue combined with the dryed and evaporated organic phase. Recrystallization from dichloromethane/ethyl acetate afforded the title compound as light brown solid (2.9 g, 81% yield). MS: m/e=420(M+H+).

Workup

additionis added over 15 minutes
temperaturethe mixture heated to 70° C. for 1 h
customAfter evaporation of the volatile components
filtrationwater, filtered
customevaporated organic phase
customRecrystallization from dichloromethane/ethyl acetate

Sources & evidence

ORD record: ord-798b081a300f48009ac522730c6f4ed2
Source dataset: uspto-grants-2003_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06620811B2

Reaction notes

Loading…