Triethylamine → HCID 67501731, compound

HRID 1631339Notes

Reaction equation

HRID 1631339 reaction equation
Cl.[NH2:2][CH2:3][C:4]([NH:7][C:8]([C:10]1[CH:11]=[N:12][N:13]2[CH:18]=[CH:17][C:16]([N:19]3[CH2:23][CH2:22][CH2:21][C@@H:20]3[C:24]3[CH:29]=[C:28]([F:30])[CH:27]=[CH:26][C:25]=3[F:31])=[N:15][C:14]=12)=[O:9])([CH3:6])[CH3:5].C(N(CC)CC)C.[CH3:39][S:40](Cl)(=[O:42])=[O:41]>C(Cl)Cl.CCOC(C)=O>[F:31][C:25]1[CH:26]=[CH:27][C:28]([F:30])=[CH:29][C:24]=1[C@H:20]1[CH2:21][CH2:22][CH2:23][N:19]1[C:16]1[CH:17]=[CH:18][N:13]2[N:12]=[CH:11][C:10]([C:8]([NH:7][C:4]([CH3:6])([CH3:5])[CH2:3][NH:2][S:40]([CH3:39])(=[O:42])=[O:41])=[O:9])=[C:14]2[N:15]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 67501201HCID 67501201, compound

Product 1

HCID 67501731HCID 67501731, compoundYield 30.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

(R)—N-(1-amino-2-methylpropan-2-yl)-5-(2-(2,5-difluorophenyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide hydrochloride (24.0 mg, 0.0532 mmol) was dissolved in DCM (0.53 mL) and triethylamine (15.2 μL, 0.109 mmol) followed by MeSO2Cl (4.34 μL, 0.0559 mmol) were added sequentially. The mixture was stirred at ambient temperature for 2 hours and was diluted with EtOAc. The mixture was washed with water and brine and was dried with MgSO4. The solution was filtered and concentrated to afford the title compound (8.0 mg, 30% yield) as a white solid. MS (apci) m/z=493.1 (M+H).

Workup

  1. additionwere added sequentially
  2. washThe mixture was washed with water and brine
  3. dry with materialwas dried with MgSO4
  4. filtrationThe solution was filtered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-d44d4ad37f964b8daa4bfa57f1d96323
Source dataset
uspto-grants-2014_07
Patent number
US08791123B2

Reaction notes

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