Triethylamine → HCID 69003138, compound

HRID 2102412Notes

Reaction equation

HRID 2102412 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[C:10]([C:19](O)=[O:20])=[N:11][C:12]3[N:13]([N:16]=[CH:17][CH:18]=3)[C:14]=2[F:15])=[C:4]([F:22])[CH:3]=1.CCN=C=NCCCN(C)C.C1C=CC2N(O)[N:41]=[N:40]C=2C=1.NN.CCN(CC)CC>CN(C=O)C.CCOC(C)=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[C:10]([C:19]([NH:40][NH2:41])=[O:20])=[N:11][C:12]3[N:13]([N:16]=[CH:17][CH:18]=3)[C:14]=2[F:15])=[C:4]([F:22])[CH:3]=1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 9321HydrazineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 69005606HCID 69005606, compound

Product 1

HCID 69003138HCID 69003138, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 6-(4-bromo-2-fluorophenylamino)-7-fluoropyrazolo[1,5-a]pyrimidine-5-carboxylic acid (1.00 equivalent), EDCI (1.50 equivalents), and HOBt (1.50 equivalents) in DMF is stirred for 30 minutes. Hydrazine (3.00 equivalents) is added followed by Et3N (2.50 equivalents). After 3 hours, the reaction mixture is diluted with EtOAc and washed with saturated NH4Cl solution, saturated NaHCO3 solution and brine. The organic layer is dried (MgSO4) and concentrated. The product is purified by flash chromatography as necessary.

Workup

  1. waitAfter 3 hours
  2. washwashed with saturated NH4Cl solution, saturated NaHCO3 solution and brine
  3. dry with materialThe organic layer is dried (MgSO4)
  4. concentrationconcentrated
  5. customThe product is purified by flash chromatography as necessary

Sources & evidence

ORD record
ord-f39f377060344832a6c654e142455154
Source dataset
uspto-grants-2009_08
Patent number
US07576072B2

Reaction notes

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