Hydroxylamine → 5-[7-(1-Ethyl-propyl)-2,5-dimethyl-pyrazolo[1,5-a]pyrimidin-3-yl]-4-trifluoromethyl-thiazol-2-ylamine

HRID 1660760Notes

Reaction equation

HRID 1660760 reaction equation
NO.CC1[N:5]([C:10]2[S:11][C:12]([C:19]3[C:20]([CH3:34])=[N:21][N:22]4[C:27]([CH:28]([CH2:31][CH3:32])[CH2:29][CH3:30])=[CH:26][C:25]([CH3:33])=[N:24][C:23]=34)=[C:13]([C:15]([F:18])([F:17])[F:16])[N:14]=2)C(C)=CC=1.C(OCC)C>C(O)(=O)C>[CH2:29]([CH:28]([C:27]1[N:22]2[N:21]=[C:20]([CH3:34])[C:19]([C:12]3[S:11][C:10]([NH2:5])=[N:14][C:13]=3[C:15]([F:16])([F:18])[F:17])=[C:23]2[N:24]=[C:25]([CH3:33])[CH:26]=1)[CH2:31][CH3:32])[CH3:30]

Participants

5

Reactant 3

HCID 787HydroxylamineHCID 3283Diethyl EtherHCID 594740583-[2-(2,5-Dimethyl-pyrrol-1-yl)-4-trifluoromethyl-thiazol-5-yl]-7-(1-ethyl-propyl)-2,5-dimethyl-pyrazolo[1,5-a]pyrimidine

Product 1

HCID 866450055-[7-(1-Ethyl-propyl)-2,5-dimethyl-pyrazolo[1,5-a]pyrimidin-3-yl]-4-trifluoromethyl-thiazol-2-ylamineYield 87%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Add hydroxylamine (2 mL, 50% in water) to a solution of 3-[2-(2,5-dimethyl-pyrrol-1-yl)-4-trifluoromethyl-thiazol-5-yl]-7-(1-ethyl-propyl)-2,5-dimethyl-pyrazolo[1,5-a]pyrimidine (1.1 g, 2.3 mmol) in acetic acid (10 mL). Heat the reaction to 80° C. for 6 h. Cool to room temperature. Pour into diethyl ether and wash with 2 M NaOH (2×) and then once with water. Dry the organic portion over sodium sulfate, filter, and concentrate to dryness under vacuum. Purify the resulting residue by silica gel chromatography (40% ethyl acetate in hexanes) to give the title compound (0.76 g, 87%). ES/MS m/z 384 (M+1)+.

Workup

  1. temperatureHeat
  2. customthe reaction to 80° C. for 6 h
  3. washwash with 2 M NaOH (2×)
  4. dry with materialDry the organic portion over sodium sulfate
  5. filtrationfilter
  6. concentrationconcentrate to dryness under vacuum
  7. customPurify the resulting residue by silica gel chromatography (40% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-a091c261ff42463b826e383fede501dd
Source dataset
uspto-grants-2011_10
Patent number
US08030304B2

Reaction notes

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