Triethylamine → HCID 67088095, compound

HRID 42994

Reaction equation

HRID 42994 reaction equation
[NH2:1][C@H:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH2:11][N:12]3[CH:16]=[C:15]([CH2:17][OH:18])[C:14]([C:19]([F:22])([F:21])[F:20])=[N:13]3)[CH:8]=2)[CH2:3]1.C(N(CC)CC)C.[O:30]1[CH:34]=[CH:33][CH:32]=[C:31]1[S:35](Cl)(=[O:37])=[O:36]>O1CCCC1.CS(C)=O>[OH:18][CH2:17][C:15]1[C:14]([C:19]([F:22])([F:21])[F:20])=[N:13][N:12]([CH2:11][C:7]2[CH:8]=[C:9]3[C:4](=[CH:5][CH:6]=2)[CH2:3][C@@H:2]([NH:1][S:35]([C:31]2[O:30][CH:34]=[CH:33][CH:32]=2)(=[O:37])=[O:36])[CH2:10]3)[CH:16]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 2795072Furan-2-sulfonyl ChlorideHCID 67026260(R)-(1-((2-amino-2,3-dihydro-1H-inden-5-yl)methyl)-3-(trifluoromethyl)-1H-pyrazol-4-yl)methanol

Product 1

HCID 67088095HCID 67088095, compoundYield 37.5%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8028TetrahydrofuranSolvent

Procedure

(R)-(1-((2-amino-2,3-dihydro-1H-inden-5-yl)methyl)-3-(trifluoromethyl)-1H-pyrazol-4-yl)methanol (0.08 mmol, 25 mg) was dissolved in tetrahydrofuran (1 mL) and triethylamine (0.25 mmol, 35 μL, 25 mg) followed by furan-2-sulfonyl chloride (0.084 mmol, 14.05 mg) and the solution stirred at room temperature overnight. The reaction was concentrated before partitioning between dichlormethane (3 mL) and 1N HCl. (3 mL). The organic layer was collected and dried using a hydrophobic frit and concentrated under a stream of nitrogen to give a brown residue which was dissolved in DMSO (1 mL) and purified on preparative basic HPLC to give (R)—N-(5-((4-(hydroxymethyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)methyl)-2,3-dihydro-1H-inden-2-yl)furan-2-sulfonamide (13.1 mg, 0.03 mmol, 37.1%) MS (ESI): m/z [M+H]+ 442.2

Workup

  1. concentrationThe reaction was concentrated
  2. custombefore partitioning between dichlormethane (3 mL) and 1N HCl
  3. customThe organic layer was collected
  4. customdried
  5. concentrationconcentrated under a stream of nitrogen
  6. customto give a brown residue which
  7. custompurified on preparative basic HPLC

Sources & evidence

ORD record
ord-78c13e640baa4b3cb2fd633cf8ea8f0a
Source dataset
uspto-grants-2013_09
Patent number
US08536214B2

Linked notes

Loading…