Triethylamine → HCID 59254936, compound

HRID 2194998Notes

Reaction equation

HRID 2194998 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][CH:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[CH:4][C:3]=1[C:16]1[N:25]=[CH:24][C:23]2[CH2:22][CH2:21][C:20]3[N:26]=[C:27]([NH:29][C:30](=[O:32])[CH3:31])[S:28][C:19]=3[C:18]=2[N:17]=1.C(N(CC)CC)C.[CH3:40][S:41](Cl)(=[O:43])=[O:42]>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][CH:10]2[CH2:11][CH2:12][N:13]([S:41]([CH3:40])(=[O:43])=[O:42])[CH2:14][CH2:15]2)=[CH:4][C:3]=1[C:16]1[N:25]=[CH:24][C:23]2[CH2:22][CH2:21][C:20]3[N:26]=[C:27]([NH:29][C:30](=[O:32])[CH3:31])[S:28][C:19]=3[C:18]=2[N:17]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 59254925HCID 59254925, compound

Product 1

HCID 59254936HCID 59254936, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 50 mg (0.11 mmol) N-[8-(2-chloro-5-piperidin-4-ylethynyl-phenyl)-4,5-dihydro-thiazolo[4,5-h]quinazolin-2-yl]-acetamide, 65 μL triethylamine and 15 μL methanesulphonic acid chloride in 1 mL dichloromethane is stirred for three hours at ambient temperature. The reaction mixture is washed with saturated aqueous sodium hydrogen carbonate solution and the organic phase is evaporated down. The residue remaining is purified by RP-HPLC. Yield: 23 mg yellow solid (MH+=542; RT=3.07; Method A)

Workup

  1. washThe reaction mixture is washed with saturated aqueous sodium hydrogen carbonate solution
  2. customthe organic phase is evaporated down
  3. customThe residue remaining is purified by RP-HPLC
  4. customYield: 23 mg yellow solid (MH+=542; RT=3.07; Method A)

Sources & evidence

ORD record
ord-a4ed67d2838a4a048f7612cd4d1c5235
Source dataset
uspto-grants-2012_12
Patent number
US08334378B2

Reaction notes

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