Chlorosuccinimide → HCID 86718888, compound

HRID 528846Notes

Reaction equation

[CH2:1]([N:3]1[C:11]2[C:6](=[CH:7][C:8]([S:12]([NH2:15])(=[O:14])=[O:13])=[CH:9][CH:10]=2)[CH:5]=[CH:4]1)[CH3:2].[Cl:16]N1C(=O)CCC1=O>>[Cl:16][C:5]1[C:6]2[C:11](=[CH:10][CH:9]=[C:8]([S:12]([NH2:15])(=[O:13])=[O:14])[CH:7]=2)[N:3]([CH2:1][CH3:2])[CH:4]=1

Participants

Reactant 2

HCID 31398Chlorosuccinimide

HCID 71062527HCID 71062527, compound2×

Product 1

HCID 86718888HCID 86718888, compoundYield 36.9%

Procedure

Following a procedure analogous to that for the synthesis of Intermediate 77, 1-ethyl-1H-indole-5-sulfonamide (Intermediate 56, 50 mg, 0.22 mmol) and N-chlorosuccinimide (36 mg, 0.27 mmol) were converted to the title compound (21 mg, 35%). 1H NMR (DMSO-d6) δ 7.99 (d, J=1.3 Hz, 1H), 7.81 (s, 1H), 7.77-7.71 (m, 1H), 7.70-7.64 (m, 1H), 7.22 (s, 2H), 4.26 (q, J=7.3 Hz, 2H), 1.36 (t, J=7.2 Hz, 3H); MS (ESI+) m/z 259.2 (M+H)+.

Sources & evidence

ORD record: ord-50597510cbbd49469061be20051508a2
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09346795B2

Reaction notes

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