Pyridine → HCID 18617644, compound

HRID 1264314Notes

Reaction equation

HRID 1264314 reaction equation
[NH2:1][CH2:2][C:3]([C:6]1[CH:27]=[CH:26][C:9]([C:10]([NH:12][CH2:13][CH2:14][C:15]2[CH:16]=[C:17]3[C:21](=[CH:22][CH:23]=2)[NH:20][CH:19]=[C:18]3[C:24]#[N:25])=[O:11])=[CH:8][CH:7]=1)([CH3:5])[CH3:4].N1C=CC=CC=1.[CH3:34][S:35](Cl)(=[O:37])=[O:36]>C(Cl)Cl>[C:24]([C:18]1[C:17]2[C:21](=[CH:22][CH:23]=[C:15]([CH2:14][CH2:13][NH:12][C:10](=[O:11])[C:9]3[CH:8]=[CH:7][C:6]([C:3]([CH3:5])([CH3:4])[CH2:2][NH:1][S:35]([CH3:34])(=[O:37])=[O:36])=[CH:27][CH:26]=3)[CH:16]=2)[NH:20][CH:19]=1)#[N:25]

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 18617788HCID 18617788, compound

Product 1

HCID 18617644HCID 18617644, compoundYield 80.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-[2-amino-1,1-dimethyl-ethyl]-N-[2-(3-cyano-1H-indol-5-yl)-ethyl]-benzamide (97 mg, 0.27 mmol) (reference example 105) in CH2Cl2 (1 ml) was added pyridine (24 μL, 0.30 mmol) and methanesulfonyl chloride (23 μL, 0.30 mmol). The reaction was stirred for 5 min then concentrated under reduced pressure. The residue was purified by flash chromatography (eluting with 8% 7M NH3 in CH3OH/CH2Cl2 to give 95 mg of product. MS (ion spray) m/z 439 (M+H)+.

Workup

  1. concentrationthen concentrated under reduced pressure
  2. customThe residue was purified by flash chromatography (
  3. washeluting with 8% 7M NH3 in CH3OH/CH2Cl2

Sources & evidence

ORD record
ord-6f1d2253417c4f389e1a2615fb334a59
Source dataset
uspto-grants-2003_04
Patent number
US06541505B1

Reaction notes

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