Triethylamine → HCID 59559681, compound

HRID 1175737Notes

Reaction equation

HRID 1175737 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.[CH3:21][S:22](Cl)(=[O:24])=[O:23].C(N(CC)CC)C>ClCCl>[CH3:21][S:22]([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:24])=[O:23]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 595597143-(2,3-dihydro-1H-indol-5-yl)-5-vinyl-3H-imidazo[4,5-b]pyridine2×

Product 1

HCID 59559681HCID 59559681, 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 (2.53 g, 9.64 mmol) (Intermediate 10.1), methanesulfonyl chloride (1.12 ml, 14.47 mmol), and triethylamine (2.94 ml, 21.22 mmol) in dichloromethane (50 ml) is stirred for 30 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 3.24 g (99%) of the respective sulfonamide. HPLC (over 10 min 10-85% MeCN/100 mM aq. NaOAc): 92% purity, tR 7.16 min (tR(SM) 6.64 min). MS (ESI) m/z (C17H16N4O2S) 341.1 (M+1, 100) 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 7.16 min (tR(SM) 6.64 min)

Sources & evidence

ORD record
ord-8cefa04febad4f658f0262fe637c2fb5
Source dataset
uspto-grants-2010_11
Patent number
US07842698B2

Reaction notes

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