Diisopropylethylamine → HCID 58056148, compound

HRID 1773596Notes

Reaction equation

HRID 1773596 reaction equation
C(N(C(C)C)CC)(C)C.[NH2:10][C:11]1[CH:24]=[C:23]([Cl:25])[CH:22]=[CH:21][C:12]=1[O:13][CH:14]1[CH2:19][CH2:18][CH:17]([OH:20])[CH2:16][CH2:15]1.[N:26]1[N:30]2[CH:31]=[N:32][CH:33]=[CH:34][C:29]2=[C:28]([C:35]([OH:37])=O)[CH:27]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C(#N)C>[Cl:25][C:23]1[CH:22]=[CH:21][C:12]([O:13][CH:14]2[CH2:19][CH2:18][CH:17]([OH:20])[CH2:16][CH2:15]2)=[C:11]([NH:10][C:35]([C:28]2[CH:27]=[N:26][N:30]3[CH:29]=[CH:34][CH:33]=[N:32][C:31]=23)=[O:37])[CH:24]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58056330HCID 58056330, compoundHCID 83678664HCID 83678664, compound

Product 1

HCID 58056148HCID 58056148, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

Diisopropylethylamine (0.35 mL, 2.01 mmol) was added at room temperature to a suspension of 4-(2-amino-4-chloro-phenoxy)-cyclohexanol (127 mg, 0.525 mmol), pyrazolo[1,5-c]pyrimidine-3-carboxylic acid (85 mg, 0.521 mmol) and HBTU (0.21 g, 0.55 mmol) in anhydrous acetonitrile (15 mL) and the resulting solution was heated at 80° C. overnight. The resulting mixture was partitioned between ethyl acetate and an aqueous solution of sodium bicarbonate (5%). The aqueous layer was extracted 3 times with ethyl acetate and the combined organic extracts were washed with brine, dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure. The brown oily residue was purified on a silica gel plug and by flash chromatography (DCM/MeOH/NH4OH) to give a pale yellow solid which was washed with dichloromethane and methanol to give 75 mg (38% yield) of pyrazolo[1,5-a]pyrimidine-3-carboxylic acid [5-chloro-2-(4-hydroxy-cyclohexyloxy)-phenyl]-amide as a white powder. MS=387 [M+H]+.

Workup

  1. customThe resulting mixture was partitioned between ethyl acetate
  2. extractionThe aqueous layer was extracted 3 times with ethyl acetate
  3. washthe combined organic extracts were washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customThe brown oily residue was purified on a silica gel plug and by flash chromatography (DCM/MeOH/NH4OH)
  8. customto give a pale yellow solid which
  9. washwas washed with dichloromethane and methanol

Sources & evidence

ORD record
ord-8776f6aa455b43a4a9e43b68880dee6c
Source dataset
uspto-grants-2016_02
Patent number
US09255110B2

Reaction notes

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