3-Chloropropanesulphonyl chloride → HCID 59559696, compound

HRID 1175739Notes

Reaction equation

HRID 1175739 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([N:10]3[C:14]4=[N:15][C:16]([CH:19]=[CH2:20])=[CH:17][CH:18]=[C:13]4[N:12]=[CH:11]3)=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[Cl:21][CH2:22][CH2:23][CH2:24][S:25](Cl)(=[O:27])=[O:26].C(N(CC)C(C)C)(C)C>ClCCl>[Cl:21][CH2:22][CH2:23][CH2:24][S:25]([N:1]1[C:9]2[C:4](=[CH:5][C:6]([N:10]3[C:14]4=[N:15][C:16]([CH:19]=[CH2:20])=[CH:17][CH:18]=[C:13]4[N:12]=[CH:11]3)=[CH:7][CH:8]=2)[CH2:3][CH2:2]1)(=[O:27])=[O:26]

Participants

5

Reactant 3

HCID 154103-Chloropropanesulphonyl chlorideHCID 81531DiisopropylethylamineHCID 595597143-(2,3-dihydro-1H-indol-5-yl)-5-vinyl-3H-imidazo[4,5-b]pyridine2×

Product 1

HCID 59559696HCID 59559696, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-(2,3-dihydro-1H-indol-5-yl)-5-vinyl-3H-imidazo[4,5-b]pyridine (270 mg, 1.03 mmol) (Intermediate 10.1), 3-chloropropanesulfonyl chloride (0.25 ml, 2.06 mmol), and N,N-diisopropylethylamine (1.08 ml, 6.18 mmol) in dichloromethane (15 ml) is stirred for 10 min at ambient temperature. The mixture is successively extracted with saturated aqueous ammonium chloride and saturated aqueous sodium bicarbonate. The organic layer is dried over sodium sulfate and concentrated in vacuo to render 351 mg (85%) of the respective sulfonamide. HPLC (over 10 min 10-85% MeCN/100 mM aq. NaOAc): 92% purity, tR 8.44 min (tR(SM) 6.59 min). MS (ESI) m/z (C19H19ClN4O2S) 403.0 (M, 100), 294.9 (65) Finnegan LCQ.

Workup

  1. extractionThe mixture is successively extracted with saturated aqueous ammonium chloride and saturated aqueous sodium bicarbonate
  2. dry with materialThe organic layer is dried over sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customHPLC (over 10 min 10-85% MeCN/100 mM aq. NaOAc)
  5. custom92% purity, tR 8.44 min (tR(SM) 6.59 min)

Sources & evidence

ORD record
ord-eab90deb5229467b9f165006522b4d5e
Source dataset
uspto-grants-2010_11
Patent number
US07842698B2

Reaction notes

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