Triethylamine → HCID 90333619, compound

HRID 595694Notes

Reaction equation

HRID 595694 reaction equation
[CH2:1]([O:8][C:9]1[C:14]([N:15]([CH3:20])[S:16]([CH3:19])(=[O:18])=[O:17])=[CH:13][N:12]2[N:21]=[C:22]([C:27]3[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=3)[C:23]([C:24](O)=[O:25])=[C:11]2[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1C=CC2N(O)N=[N:40][C:38]=2C=1.CCN=C=NCCCN(C)C.CN.Cl.CCN(CC)CC>CN(C=O)C>[CH2:1]([O:8][C:9]1[C:14]([N:15]([CH3:20])[S:16]([CH3:19])(=[O:18])=[O:17])=[CH:13][N:12]2[N:21]=[C:22]([C:27]3[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=3)[C:23]([C:24]([NH:40][CH3:38])=[O:25])=[C:11]2[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 6364545Methylamine hydrochlorideHCID 90333589HCID 90333589, compound

Product 1

HCID 90333619HCID 90333619, compoundYield 97.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-(benzyloxy)-2-(4-fluorophenyl)-6-(N-methylmethylsulfonamido)pyrazolo[1,5-a]pyridine-3-carboxylic acid (3 g, 6.4 mmol), HOBT (1.3 g, 9.6 mmol) and EDCI (2.5 g, 12.8 mmol) in DMF (50 mL) was allowed to stir at room temperature. After 30 minutes, CH3NH2.HCl (857 mg, 12.8 mmol) and Et3N (1.3 g, 12.8 mmol) were added to the mixture, and the mixture was allowed to stir overnight at room temperature. After the solvent was removed, H2O and NaHCO3 (aq.) were added and the mixture was stirred at room temperature for 1 hour. After filtration, the cake was washed with H2O and dried to give pure 5-(benzyloxy)-2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)pyrazolo[1,5-a]pyridine-3-carboxamide (3 g, yield: 97%). 1H-NMR (CDCl3, 400 MHz) δ 8.43 (s, 1H), 7.86 (s, 1H), 7.56˜7.59 (m, 2H), 7.35˜7.44 (m, 5H), 7.16 (t, J=8.8 Hz, 2H), 5.41 (br s, 1H), 5.15 (s, 2H), 3.22 (s, 3H), 2.77 (d, J=4.8 Hz, 3H), 2.71 (s, 3H). MS (M+H)+: 483.

Workup

  1. stirringto stir overnight at room temperature
  2. customAfter the solvent was removed
  3. additionH2O and NaHCO3 (aq.) were added
  4. stirringthe mixture was stirred at room temperature for 1 hour
  5. filtrationAfter filtration
  6. washthe cake was washed with H2O
  7. customdried

Sources & evidence

ORD record
ord-ea94ecf92c6e4cfaa3767387cb5764dd
Source dataset
uspto-grants-2016_01
Patent number
US09243002B2

Reaction notes

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