Triethylamine → HCID 178434620, compound

HRID 2215314Notes

Reaction equation

HRID 2215314 reaction equation
[CH3:1][S:2]([Cl:5])(=[O:4])=[O:3].[Cl:6][C:7]1[CH:8]=[C:9]([CH:12]=[C:13]([O:15][C:16]2[C:17]([CH3:28])=[N:18][NH:19][C:20]=2[CH2:21][N:22]2[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)[CH:14]=1)[C:10]#[N:11].C(N(CC)CC)C>ClCCl>[Cl:5][CH2:7][Cl:6].[CH3:13][OH:15].[NH3:11].[Cl:6][C:7]1[CH:8]=[C:9]([CH:12]=[C:13]([O:15][C:16]2[C:17]([CH3:28])=[N:18][NH:19][C:20]=2[CH2:21][N:22]2[CH2:23][CH2:24][N:25]([S:2]([CH3:1])(=[O:4])=[O:3])[CH2:26][CH2:27]2)[CH:14]=1)[C:10]#[N:11]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 178434619HCID 178434619, compound

Product 2

HCID 21584172Ammonia methanol dichloromethaneHCID 178434620HCID 178434620, compoundYield 132.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methanesulphonyl chloride (19 μl, 0.240 mmol) was added dropwise to a stirred solution of the amine of Example 78 (80 mg, 0.240 mmol) and triethylamine (45 μL, 0.288 mmol) in dichloromethane (3 ml) at room temperature under nitrogen. The reaction was stirred for 30 minutes and then concentrated under reduced pressure to leave a yellow oil. The crude product was purified by flash column chromatography on silica gel eluting with dichloromethane and then dichloromethane:methanol:ammonia (95:4:1, by volume) to provide the title compound (65 mg) as a white foam.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customto leave a yellow oil
  3. customThe crude product was purified by flash column chromatography on silica gel eluting with dichloromethane

Sources & evidence

ORD record
ord-06c5a947fe65414cacf6d20e0b5ca17c
Source dataset
uspto-grants-2006_09
Patent number
US07109228B2

Reaction notes

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