Triethylamine → HCID 58975180, compound

HRID 737027Notes

Reaction equation

HRID 737027 reaction equation
[F:1][C:2]1[CH:21]=[CH:20][C:5]([CH2:6][NH:7][C:8]([C:10]2[CH:15]=[CH:14][C:13]([S:16](Cl)(=[O:18])=[O:17])=[CH:12][CH:11]=2)=[O:9])=[CH:4][CH:3]=1.[NH:22]1[C:26]2=[N:27][CH:28]=[CH:29][CH:30]=[C:25]2[CH:24]=[CH:23]1.N1(C2C=CN=CC=2)CCCC1.C(N(CC)CC)C>CC#N>[F:1][C:2]1[CH:21]=[CH:20][C:5]([CH2:6][NH:7][C:8](=[O:9])[C:10]2[CH:15]=[CH:14][C:13]([S:16]([N:22]3[C:26]4=[N:27][CH:28]=[CH:29][CH:30]=[C:25]4[CH:24]=[CH:23]3)(=[O:18])=[O:17])=[CH:12][CH:11]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 92221H-Pyrrolo(2,3-b)pyridineHCID 755674-PyrrolidinopyridineHCID 589751254-(4-Fluoro-benzylcarbamoyl)-benzenesulfonyl chloride

Product 1

HCID 58975180HCID 58975180, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Add MeCN (2 ml) to a flask under N2 containing 4-(4-Fluoro-benzylcarbamoyl)-benzenesulfonyl chloride (50 mg, 0.152 mmol), 1H-pyrrolo[2,3-b]pyridine (18 mg, 0.152 mmol), 4-Pyrrolidin-1-yl-pyridine (2 mg, 0.167 mmol), and triethylamine (17 mg, 0.167 mmol). Heat reaction to 80° C. for 16 hours. Cool the solution to room temperature, remove MeCN on rotovap. Purify crude material on silica gel to give 45 mg (73% yield) of N-(4-Fluoro-benzyl)-4-(pyrrolo[2,3-b]pyridine-1-sulfonyl)-benzamide. Mass Spectrum (m/e): 410.1 (M+).

Workup

  1. temperatureHeat
  2. customreaction to 80° C. for 16 hours
  3. customremove MeCN on rotovap
  4. customPurify crude material on silica gel

Sources & evidence

ORD record
ord-629d8914a3d0424185fd1cd220209027
Source dataset
uspto-grants-2009_09
Patent number
US07595339B2

Reaction notes

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