Methanol → HCID 68545577, compound

HRID 731752Notes

Reaction equation

HRID 731752 reaction equation
CO.C([Cl:6])(C)=O.[CH2:7]([NH:14][CH2:15][CH:16]([CH3:31])[C:17]([C:19]1[C:20]([CH:28]([CH3:30])[CH3:29])=[N:21][N:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=12)=[O:18])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>CCOCC>[ClH:6].[CH2:7]([NH:14][CH2:15][CH:16]([CH3:31])[C:17]([C:19]1[C:20]([CH:28]([CH3:30])[CH3:29])=[N:21][N:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=12)=[O:18])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 887Methanol2×HCID 6367Acetyl chlorideHCID 57837464HCID 57837464, compound

Product 1

HCID 68545577HCID 68545577, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To MeOH (2 mL) cooled in an ice bath under argon was added AcCl (0.047 mL) dropwise. This solution was stirred for 10 minutes before adding dropwise to 3-(benzylamino)-1-(2-isopropylpyrazolo[1,5-a]pyridin-3-yl)-2-methylpropan-1-one (0.200 g) in dry Et2O (5 mL), which was also cooled in an ice bath. The solvent was evaporated and the residue was treated with hexane (1 ml). the solvent was evaporated and a yellow solid was obtained. This solid was stirred in 10 mL of a solution containing MeOH (1%) and Et2O (99%) for 8 hours. The solid was filtered, washed with Et2O and dried under reduced pressure to afford 172 mg of 3-(benzylamino)-1-(2-isopropylpyrazolo[1,5-a]pyridin-3-yl)-2-methylpropan-1-one hydrochloride as a pale yellow solid. mp=171-175° C. (Et2O, pentane), IR (KBr) v=3428, 3034, 2965, 2784, 25589, 2425, 1642, 1538, 1507, 1481, 1440, 1360, 1264, 1210, 1188, 972; 1H NMR (600 MHz, DMSO-d6) δ=9.60 (bs, 1H), 9.23 (bs, 1H), 8.86 (d, J=6.8 Hz, 1H), 8.09 (d, J=9.1 Hz, 1H), 7.56-7.68 (m, 3H), 7.37-7.47 (m, 3H), 7.15 (tr, J=6.8 Hz, 1H), 4.15-4.23 (m, 2H), 3.87-3.95 (m, 1H), 3.74 (sept, J=6.8 Hz, 1H), 3.34-3.42 (m, 1H), 2.94-3.01 (m, 1H), 1.33 (d, J=6.8 Hz, 3H), 1.28 (d, J=6.8 Hz, 3H), 1.22 (d, J=7.6 Hz, 3H); 13C NMR (150 MHz, CDCl3) δ=194.8, 164.4, 140.9, 132.3, 130.7, 130.6, 129.6, 129.4, 129.0, 118.7, 114.7, 107.4, 48.2, 41.3, 27.6, 22.9, 22.3, 17.1; MS (FAB) m/z 337 (M+1, 25.5), 336 (M+, 100.0), 218 (16.7), 217 (99.6), 187 (28.1), 173 (17.8), 161 (13.1), 120 (31.9); HRMS (FAB) calcd for C21H26N3O: 336.2076; found: 336.2066. Compound 1066.

Workup

  1. temperaturewas also cooled in an ice bath
  2. customThe solvent was evaporated
  3. additionthe residue was treated with hexane (1 ml)
  4. customthe solvent was evaporated
  5. customa yellow solid was obtained
  6. filtrationThe solid was filtered
  7. washwashed with Et2O
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-e16d0026830e48228ea67470c5914a64
Source dataset
uspto-grants-2009_09
Patent number
US07585875B2

Reaction notes

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