Triethylamine → HCID 59835833, compound

HRID 1916677Notes

Reaction equation

HRID 1916677 reaction equation
[CH2:1]([N:3]([CH2:6][CH3:7])[CH2:4][CH3:5])[CH3:2].[CH3:8][S:9](Cl)(=[O:11])=[O:10].[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:21]=[CH:22][C:23]([C:26]#[C:27][C:28]3[CH:29]=[C:30]4[C:35](=[CH:36][CH:37]=3)[N:34](C)C(N3CCCC3)[CH2:32][CH2:31]4)=[N:24][CH:25]=2)=[CH:16][CH:15]=1>C(Cl)Cl>[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:21]=[CH:22][C:23]([C:26]#[C:27][C:28]3[CH:29]=[C:30]4[C:35](=[CH:36][CH:37]=3)[N:34]([S:9]([CH3:8])(=[O:11])=[O:10])[CH:2]([CH2:1][N:3]3[CH2:6][CH2:7][CH2:5][CH2:4]3)[CH2:32][CH2:31]4)=[N:24][CH:25]=2)=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chloride2×HCID 69074167HCID 69074167, compound

Product 1

HCID 59835833HCID 59835833, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.13 mL (0.93 mmol) triethylamine and 36 μL (0.47 mmol) methanesulphonic acid chloride are added successively at 0° C. to a solution of 200 mg (0.47 mmol) 6-[5-(4-chloro-phenyl)-pyridin-2-ylethynyl]-2-pyrrolidin-1-yl methyl-1,2,3,4-tetrahydro-quinoline (see Example 3.46) in 5 mL DCM. The reaction mixture is heated to RT and stirred for a further hour at this temperature. Another 36 μL (0.47 mmol) methanesulphonic acid chloride are added and the mixture is stirred for a further hour at RT. The reaction mixture is poured onto water and exhaustively extracted with DCM. The organic phase is dried over MgSO4 and the solvent is eliminated i.vac. The purification is carried out by column chromatography using HPLC-MS.

Workup

  1. stirringthe mixture is stirred for a further hour at RT
  2. additionThe reaction mixture is poured onto water
  3. extractionexhaustively extracted with DCM
  4. dry with materialThe organic phase is dried over MgSO4
  5. customThe purification

Sources & evidence

ORD record
ord-fa2aef3c95bf49e48a29e5cc198b4262
Source dataset
uspto-grants-2013_12
Patent number
US08618132B2

Reaction notes

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