Diisopropylethylamine → N-(4-(4,5,6,7-tetrahydrobenzothiazol-6-ylamino)butyl)benzothiazole-2-carboxamide

HRID 1942383Notes

Reaction equation

O[CH2:2][CH2:3][CH2:4][CH2:5][NH:6][C:7]([C:9]1[S:10][C:11]2[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=2[N:13]=1)=[O:8].[S:18]1[C:22]2[CH2:23][CH:24]([NH2:27])[CH2:25][CH2:26][C:21]=2[N:20]=[CH:19]1.CCN(C(C)C)C(C)C.[I-].C(C[P+](C)(C)C)#N.C([O-])(O)=O.[Na+]>C(#N)CC.C(Cl)Cl>[S:18]1[C:22]2[CH2:23][CH:24]([NH:27][CH2:2][CH2:3][CH2:4][CH2:5][NH:6][C:7]([C:9]3[S:10][C:11]4[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=4[N:13]=3)=[O:8])[CH2:25][CH2:26][C:21]=2[N:20]=[CH:19]1

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of 339 mg (1.4 mmol) N-(4-hydroxybutyl)benzothiazole-2-carboxamide, 198 mg (1.2 mmol) 4,5,6,7-tetrahydro-benzothiazol-6-yl-amine and 210 mg (1.6 mmol) DIPEA in 6 mL of propionitrile is added 0.39 g (1.6 mmol) cyanomethyltrimethylphosphonium iodide under argon. The mixture is heated for 2 hours at 90° C. After cooling down to room temperature 10 mL of saturated NaHCO3 solution and 20 mL of CH2Cl2 are added. The organic phase is extracted with 10 mL of water three times. After drying and removing of the solvent in vacuum the brown oil received is purified via silica gel chromatography.

Workup

additionare added
extractionThe organic phase is extracted with 10 mL of water three times
customAfter drying
customremoving of the solvent in vacuum the brown oil
customreceived is purified via silica gel chromatography

Sources & evidence

ORD record: ord-d42f12f0e1f4473689863671b910d587
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08389555B2

Reaction notes

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