Triethylamine → HCID 68514809, compound

HRID 2063252Notes

Reaction equation

HRID 2063252 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]2[C:9]([C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=3)=[N:10][N:11]3[CH2:16][CH2:15][CH2:14][CH2:13][C:12]=23)[CH:5]=[CH:4][N:3]=1.C(N(CC)CC)C.[CH:31]1([NH2:35])[CH2:34][CH2:33][CH2:32]1>ClCCl>[CH:31]1([NH:35][C:2]2[N:7]=[C:6]([C:8]3[C:9]([C:17]4[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=4)=[N:10][N:11]4[CH2:16][CH2:15][CH2:14][CH2:13][C:12]=34)[CH:5]=[CH:4][N:3]=2)[CH2:34][CH2:33][CH2:32]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 75645CyclobutylamineHCID 86646911HCID 86646911, compound2×

Product 1

HCID 68514809HCID 68514809, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of 3-(2-chloro-4-pyrimidinyl)-2-(4-fluorophenyl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyridine (i.e. the product of Step B) (200 mg, 0.54 mmol), triethylamine (55 mg, 0.54 mmol) and cyclobutylamine (5.0 mL) was stirred at 65° C. for 18 h. The reaction mixture was diluted with dichloromethane (50 mL) and treated with silica gel (20.0 g). The silica gel suspension was concentrated under reduced pressure to leave a mixture of silica gel and crude product, which was purified by silica gel chromatography using a gradient of ethyl acetate/hexanes (1:9 to 1:0) as eluant to give 70 mg of the title product, a compound of the present invention, as a white solid.

Workup

  1. additiontreated with silica gel (20.0 g)
  2. concentrationThe silica gel suspension was concentrated under reduced pressure
  3. customto leave
  4. additiona mixture of silica gel and crude product, which
  5. customwas purified by silica gel chromatography

Sources & evidence

ORD record
ord-95c18468cd984c91a3b95eea290e72b0
Source dataset
uspto-grants-2012_10
Patent number
US08288375B2

Reaction notes

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