199292-93-8 → HCID 10304198, compound

HRID 967382Notes

Reaction equation

HRID 967382 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([CH:10]3[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]3)=[N:7][C:6]=2[CH:16]=1.[O:17]1[CH2:19][CH:18]1[CH2:20][N:21]1[C:29]2[CH2:28][CH2:27][N:26]([C:30](=[O:32])[CH3:31])[CH2:25][C:24]=2[C:23]([C:33]2[CH:38]=[CH:37][C:36]([C:39]([F:42])([F:41])[F:40])=[CH:35][CH:34]=2)=[N:22]1>CCO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([CH:10]3[CH2:11][CH2:12][N:13]([CH2:19][CH:18]([OH:17])[CH2:20][N:21]4[C:29]5[CH2:28][CH2:27][N:26]([C:30](=[O:32])[CH3:31])[CH2:25][C:24]=5[C:23]([C:33]5[CH:38]=[CH:37][C:36]([C:39]([F:42])([F:41])[F:40])=[CH:35][CH:34]=5)=[N:22]4)[CH2:14][CH2:15]3)=[N:7][C:6]=2[CH:16]=1

Participants

4

Reactant 2

HCID 22293687199292-93-8HCID 222938171-[1-Oxiranylmethyl-3-(4-trifluoromethyl-phenyl)-1,4,6,7-tetrahydro-pyrazolo[4,3-c]pyridin-5-yl]-ethanone

Product 1

HCID 10304198HCID 10304198, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 130 mg (0.55 mmol) of 5-chloro-2-piperidin-4-yl-benzooxazole was dissolved in 4 mL EtOH and treated with 100 mg (0.27 mmol) of 1-[1-oxiranylmethyl-3-(4-trifluoromethyl-phenyl)-1,4,6,7-tetrahydro-pyrazolo[4,3-c]pyridin-5-yl]-ethanone. The solution was heated to 60° C. overnight. The solvent was then removed by rotary evaporation and the crude product was purified by column chromatography (silica, 0-10% MeOH/EtOAc) to afford 156 mg (95%) of a white solid. MS (electrospray): exact mass calculated for C30H31ClF3N5O3, 601.21. m/z found, 602.2 [M+H]+. 1H NMR (CDCl3, 400 MHz, a mixture of amide rotamers):7.76 (d, J=8.41 Hz, 1H), 7.71 and 7.67 (A and B of AB quartet, J=8.41 Hz, 2H), 7.65-7.61 (m, 2H), 7.38 (d, J=8.61 Hz, 1H), 7.26 (dd, J=8.61, 1.96, 1H), 4.86 and 4.74 (A and B of AB quartet, J=15.65 Hz, 1H), 4.64 (br s, 1H), 4.24-4.10 (m, 2.3H), 4.07-3.97 (m, 1.7H), 3.89-3.67 (m, 2H), 3.06-3.00 (m, 1H), 3.00-2.90 (m, 2H), 2.90-2.74 (m, 2H), 2.51-2.38 (m, 3H), 2.25-2.10 (m, 2.3H), 2.20 (s, 1.5H), 2.15 (s, 1.5H), 2.06-1.83 (m, 2.7H).

Workup

  1. customThe solvent was then removed by rotary evaporation
  2. customthe crude product was purified by column chromatography (silica, 0-10% MeOH/EtOAc)

Sources & evidence

ORD record
ord-0f61a18c3e444d7983646c4a70010eff
Source dataset
uspto-grants-2005_10
Patent number
US06953793B2

Reaction notes

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