Acetonitrile → HCID 59432880, compound

HRID 1809332Notes

Reaction equation

[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[NH:6][S:7]([C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[NH:15][CH2:14][CH2:13]2)(=[O:9])=[O:8].C(N(CC)CC)C.[Cl:26][CH2:27][C:28](Cl)=[O:29].CC#N>CN(C=O)C>[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[NH:6][S:7]([C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[N:15]([C:28](=[O:29])[CH2:27][Cl:26])[CH2:14][CH2:13]2)(=[O:9])=[O:8]

Participants

Conditions

Temperature: -75 °C

Procedure

To a stirring solution of 2,3-dihydro-1H-indole-5-sulfonic acid thiazol-2-ylamide (2.35 g, 8.36 mmol) in DMF (10 mL), at −75° C., was added triethylamine (1.16 mL, 8.36 mmol) followed by chloroacetyl chloride (1.88 g, 16.7 mmol). The mixture was stirred at −75° C. for 1 h. The reaction showed product formation by LC/MS (10-99% CH3CN). After quenching with MeOH and allowing the mixture to warm to room temperature, the solvents were removed in vacuo. The mixture was purified via column chromatography (2% MeOH in CH2Cl2) to obtain the desired amide (1.95 g, 5.9 mmol, 70% yield). LC/MS (10-99% CH3CN), M/Z: M+1 obs=359.3; tR=2.46 min.

Workup

customAfter quenching with MeOH
temperatureto warm to room temperature
customthe solvents were removed in vacuo
customThe mixture was purified via column chromatography (2% MeOH in CH2Cl2)

Sources & evidence

ORD record: ord-88562fa45a784e49a687aae3d18bf639
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08362032B2

Reaction notes

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