Isopropylamine → HCID 42623662, compound

HRID 2063253Notes

Reaction equation

HRID 2063253 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.[CH:24]([NH2:27])([CH3:26])[CH3:25]>ClCCl>[F:23][C:20]1[CH:21]=[CH:22][C:17]([C:9]2[C:8]([C:6]3[CH:5]=[CH:4][N:3]=[C:2]([NH:27][CH:24]([CH3:26])[CH3:25])[N:7]=3)=[C:12]3[CH2:13][CH2:14][CH2:15][CH2:16][N:11]3[N:10]=2)=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 6363IsopropylamineHCID 86646911HCID 86646911, compound2×

Product 1

HCID 42623662HCID 42623662, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
34 °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) and isopropylamine (5.0 mL) was stirred at 34° 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 115 mg of the title product, a compound of the present invention, as an off-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-421e10f8d2d145e78249bf7b050194cd
Source dataset
uspto-grants-2012_10
Patent number
US08288375B2

Reaction notes

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