Isopropylamine → 4-[2-(Phenyl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl]-N-isopropylpyridine-2-amine

HRID 1890254Notes

Reaction equation

HRID 1890254 reaction equation
F[C:2]1[CH:7]=[C:6]([C:8]2[C:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[N:11][N:10]3[CH2:19][CH2:20][CH2:21][C:9]=23)[CH:5]=[CH:4][N:3]=1.[CH:22]([NH2:25])([CH3:24])[CH3:23]>>[C:13]1([C:12]2[C:8]([C:6]3[CH:5]=[CH:4][N:3]=[C:2]([NH:25][CH:22]([CH3:24])[CH3:23])[CH:7]=3)=[C:9]3[CH2:21][CH2:20][CH2:19][N:10]3[N:11]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

3

Reactant 2

HCID 6363IsopropylamineHCID 674388563-(2-fluoropyridin-4-yl)-2-phenyl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole

Product 1

HCID 674383304-[2-(Phenyl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl]-N-isopropylpyridine-2-amine

Conditions

Temperature
140 °C

Procedure

In an autoclave, a mixture of 1.10 g (0.39 mmol) of 3-(2-fluoropyridin-4-yl)-2-phenyl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole and 1.5 ml of isopropylamine is heated at 140° C. After 16 h, the reaction mixture is concentrated under reduced pressure. After purification by column chromatography on silica gel (cyclohexane/ethyl acetate), 50 mg (35%) of the desired product are obtained; log P(HCOOH): 1.21; 1H-NMR (DMSO-d6): 7.81 (d, 1H), 7.36 (m, 5H), 6.28 (s, 1H), 6.21 (m, 2H), 4.15 (dd, 2H), 3.84 (m, 1H), 2.98 (dd, 2H), 2.59 (m, 2H), 1.08 (d, 6H).

Workup

  1. concentrationthe reaction mixture is concentrated under reduced pressure
  2. customAfter purification by column chromatography on silica gel (cyclohexane/ethyl acetate), 50 mg (35%) of the desired product
  3. customare obtained

Sources & evidence

ORD record
ord-91c96f8587154aaa87be2b9bc4cd267c
Source dataset
uspto-grants-2013_08
Patent number
US08507472B2

Reaction notes

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