Piperidine → 2-[1-(4-Ethoxy-2,6-difluorobenzyl)-1,4,5,6-tetrahydrocyclopenta-[c]pyrazol-3-yl]-5-methoxypyrimidin-4-amine

HRID 1482924Notes

Reaction equation

HRID 1482924 reaction equation
[CH2:1]([O:3][C:4]1[CH:21]=[C:20]([F:22])[C:7]([CH2:8][N:9]2[C:13]3[CH2:14][CH2:15][CH2:16][C:12]=3[C:11]([C:17](=[NH:19])[NH2:18])=[N:10]2)=[C:6]([F:23])[CH:5]=1)[CH3:2].N1CCCCC1.C[N:31](C)[CH:32](N(C)C)[CH:33]([O:36][CH3:37])[C:34]#N>>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([F:23])[C:7]([CH2:8][N:9]2[C:13]3[CH2:14][CH2:15][CH2:16][C:12]=3[C:11]([C:17]3[N:18]=[C:32]([NH2:31])[C:33]([O:36][CH3:37])=[CH:34][N:19]=3)=[N:10]2)=[C:20]([F:22])[CH:21]=1)[CH3:2]

Participants

4

Reactant 3

HCID 8082PiperidineHCID 129674413,3-Bis(dimethylamino)-2-methoxypropanenitrileHCID 900127521-(4-Ethoxy-2,6-difluorobenzyl)-1,4,5,6-tetrahydrocyclopenta[c]-pyrazole-3-carboximidamide

Product 1

HCID 900126782-[1-(4-Ethoxy-2,6-difluorobenzyl)-1,4,5,6-tetrahydrocyclopenta-[c]pyrazol-3-yl]-5-methoxypyrimidin-4-amine

Conditions

Temperature
100 °C

Procedure

4.21 g of 1-(4-ethoxy-2,6-difluorobenzyl)-1,4,5,6-tetrahydrocyclopenta[c]-pyrazole-3-carboximidamide 1-2-1 (13.2 mmol, 1.00 eq.) were suspended in 47 mL of dry 3-methyl-1 butanole, 0.26 mL of piperidine (2.63 mmol, 0.20 eq.) and 3.09 g of 3,3-bis(dimethylamino)-2-methoxypropanenitrile 1-3-1 (18.0 mmol, 1.37 eq.) were added under nitrogen atmosphere and stirred over night at 100° C. bath temperature. The reaction mixture was cold with an ice bath the precipitate was filtered of, washed with 3-methyl-1 butanol and dried at 50° C. to give 1.77 g (4.41 mmol, 33.5%) of analytically pure target compound.

Workup

  1. additionwere added under nitrogen atmosphere
  2. customThe reaction mixture was cold with an ice bath
  3. filtrationthe precipitate was filtered of,
  4. washwashed with 3-methyl-1 butanol
  5. customdried at 50° C.
  6. customto give 1.77 g (4.41 mmol, 33.5%) of analytically pure target compound

Sources & evidence

ORD record
ord-6e1cd594986743a0b26b34966495bc9d
Source dataset
uspto-grants-2016_08
Patent number
US09416125B2

Reaction notes

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