Triethylamine → HCID 59333527, compound

HRID 421385Notes

Reaction equation

HRID 421385 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[CH2:6]([C@@H:8]1[NH:13][CH2:12][CH2:11][N:10]([C:14]2[N:15]([CH2:36][C:37]([F:40])([F:39])[F:38])[C:16]3[C:21]([N:22]=2)=[C:20]([N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)[N:19]=[C:18]([C:29]2[CH:30]=[N:31][C:32]([NH2:35])=[N:33][CH:34]=2)[N:17]=3)[CH2:9]1)[CH3:7].C(N(CC)CC)C>C(Cl)Cl>[CH2:6]([C@@H:8]1[N:13]([S:2]([CH3:1])(=[O:4])=[O:3])[CH2:12][CH2:11][N:10]([C:14]2[N:15]([CH2:36][C:37]([F:40])([F:39])[F:38])[C:16]3[C:21]([N:22]=2)=[C:20]([N:23]2[CH2:24][CH2:25][O:26][CH2:27][CH2:28]2)[N:19]=[C:18]([C:29]2[CH:34]=[N:33][C:32]([NH2:35])=[N:31][CH:30]=2)[N:17]=3)[CH2:9]1)[CH3:7]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 593335585-{8-[(3S)-3-Ethylpiperazin-1-yl]-6-morpholin-4-yl-9-(2,2,2-trifluoroethyl)-9H-purin-2-yl}pyrimidin-2-amine

Product 1

HCID 59333527HCID 59333527, compoundYield 68.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methanesulfonyl chloride (0.022 ml, 0.28 mmol) was added dropwise to a methylene chloride solution (6 ml) of 5-{8-[(3S)-3-ethylpiperazin-1-yl]-6-morpholin-4-yl-9-(2,2,2-trifluoroethyl)-9H-purin-2-yl}pyrimidin-2-amine (107 mg, 0.22 mmol) and triethylamine (0.061 ml, 0.44 mmol) with ice cooling and the resulting mixture was stirred at the same temperature for 2 hours. The resulting mixture was partitioned with ethyl acetate and saturated aqueous ammonium chloride solution and the organic layer was washed with saturated brine and dried over anhydrous sodium sulfate, the mixture was filtrated, the filtrate was concentrated under reduced pressure, and the resulting residue was purified by preparative thin layer silica gel chromatography (chloroform:methanol=95:5) to give the title compound (86 mg) as a pale yellow solid.

Workup

  1. customThe resulting mixture was partitioned with ethyl acetate and saturated aqueous ammonium chloride solution
  2. washthe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationthe mixture was filtrated
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customthe resulting residue was purified by preparative thin layer silica gel chromatography (chloroform:methanol=95:5)

Sources & evidence

ORD record
ord-b0280a819ff34559855ae43581ed7bfd
Source dataset
uspto-grants-2012_01
Patent number
US08097622B2

Reaction notes

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