Chloroacetyl chloride → HCID 86691395, compound

HRID 540163Notes

Reaction equation

[O:1]=[S:2]1(=[O:25])[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[CH2:6][N:5]([C:13]2[CH:22]=[C:21]([NH2:23])[C:20]3[C:15](=[CH:16][CH:17]=[C:18]([CH3:24])[CH:19]=3)[N:14]=2)[CH2:4][CH2:3]1.N12CCCN=C1CCCCC2.[Cl:37][CH2:38][C:39](Cl)=[O:40]>C(Cl)(Cl)Cl.C(OCC)(=O)C>[Cl:37][CH2:38][C:39]([NH:23][C:21]1[C:20]2[C:15](=[CH:16][CH:17]=[C:18]([CH3:24])[CH:19]=2)[N:14]=[C:13]([N:5]2[CH2:6][C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[S:2](=[O:1])(=[O:25])[CH2:3][CH2:4]2)[CH:22]=1)=[O:40]

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of 2-(1,1-dioxido-2,3-dihydro-1,4-benzothiazepin-4(5H)-yl)-6-methylquinolin-4-amine (500 mg, 1.4 mmol) in chloroform (10 mL) was added 1,8-diazabicyclo[5.4.0]undec-7-ene (0.41 mL, 2.8 mmol) followed by chloroacetyl chloride (0.17 mL, 2.1 mmol) at room temperature. The resulting solution was heated with stirring at 70° C. for 2 hours under nitrogen. After being cooled to room temperature, the reaction was diluted with ethyl acetate (50 mL), washed with water (50 mL×3), dried over sodium sulfate and concentrated in vacuo. The residue was purified by column chromatography on silica gel (eluting with 25% ethyl acetate in petroleum ether) to give 120 mg of the product as an off-white solid.

Workup

temperatureThe resulting solution was heated
temperatureAfter being cooled to room temperature
washwashed with water (50 mL×3)
dry with materialdried over sodium sulfate
concentrationconcentrated in vacuo
customThe residue was purified by column chromatography on silica gel (eluting with 25% ethyl acetate in petroleum ether)

Sources & evidence

ORD record: ord-4f497adae67b45a78f7a5ec0996bc9e4
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08871756B2

Reaction notes

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