1-Hydroxybenzotriazole → HCID 58056354, compound

HRID 1773603Notes

Reaction equation

HRID 1773603 reaction equation
C(N(C(C)C)CC)(C)C.[NH2:10][C:11]1[CH:12]=[C:13](/[CH:19]=[CH:20]/[CH2:21][OH:22])[CH:14]=[CH:15][C:16]=1[O:17][CH3:18].[N:23]1[N:27]2[CH:28]=[CH:29][CH:30]=[N:31][C:26]2=[C:25]([C:32](O)=[O:33])[CH:24]=1.C1C=CC2N(O)N=NC=2C=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C(#N)C>[OH:22][CH2:21]/[CH:20]=[CH:19]/[C:13]1[CH:14]=[CH:15][C:16]([O:17][CH3:18])=[C:11]([NH:10][C:32]([C:25]2[CH:24]=[N:23][N:27]3[CH:28]=[CH:29][CH:30]=[N:31][C:26]=23)=[O:33])[CH:12]=1

Participants

7

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 1910189Pyrazolo[1,5-a]pyrimidine-3-carboxylic acidHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58056219HCID 58056219, compound

Product 1

HCID 58056354HCID 58056354, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of diisopropylethylamine (0.25 mL), (E)-3-(3-amino-4-methoxy-phenyl)-prop-2-en-1-ol (90 mg), pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (65 mg), HOBT (85 mg) and HBTU (0.20 g) in anhydrous acetonitrile (5 mL) was heated to 80° C. overnight. The resulting mixture was evaporated under reduced pressure and the residue was partitioned between ethyl acetate and water. The organic layer was separated, washed with brine, dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure. The crude residue was purified by flash chromatography (MeOH/EtOAc, 3/97) to give an oil. This residue was triturated with ethyl acetate to give, upon standing for 1 hour, 20 mg of (E)-3-(3-amino-4-methoxy-phenyl)-prop-2-en-1-ol as a light brown solid which was collected by filtration. MS=325 [M+H]+.

Workup

  1. customThe resulting mixture was evaporated under reduced pressure
  2. customthe residue was partitioned between ethyl acetate and water
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customevaporated under reduced pressure
  8. customThe crude residue was purified by flash chromatography (MeOH/EtOAc, 3/97)
  9. customto give an oil
  10. customThis residue was triturated with ethyl acetate
  11. customto give
  12. filtration20 mg of (E)-3-(3-amino-4-methoxy-phenyl)-prop-2-en-1-ol as a light brown solid which was collected by filtration

Sources & evidence

ORD record
ord-1e8cb08da61c4015be30f048ebb74016
Source dataset
uspto-grants-2016_02
Patent number
US09255110B2

Reaction notes

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