Diisopropylamine → HCID 69005606, compound

HRID 2102407Notes

Reaction equation

HRID 2102407 reaction equation
N(C(C)C)C(C)C.[Li]CCCC.[Br:13][C:14]1[CH:19]=[CH:18][C:17]([NH2:20])=[C:16]([F:21])[CH:15]=1.Cl[C:23]1[C:24]([C:33]([OH:35])=[O:34])=[N:25][C:26]2[N:27]([N:30]=[CH:31][CH:32]=2)[C:28]=1[F:29]>C1COCC1>[Br:13][C:14]1[CH:19]=[CH:18][C:17]([NH:20][C:23]2[C:24]([C:33]([OH:35])=[O:34])=[N:25][C:26]3[N:27]([N:30]=[CH:31][CH:32]=3)[C:28]=2[F:29])=[C:16]([F:21])[CH:15]=1

Participants

6

Reactant 4

HCID 7912DiisopropylamineHCID 1230504-Bromo-2-fluoroanilineHCID 59519496HCID 59519496, compoundHCID 178418339Butyllithium

Product 1

HCID 69005606HCID 69005606, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a solution of i-Pr2NH (3.50 equivalents) in THF at 0° C. is added n-BuLi (3.50 equivalents, 2.5 M solution in hexanes). After stirring 15 minutes, the mixture is cooled to −78° C. 4-Bromo-2-fluorophenylamine (2.50 equivalents) is added. After vigorous stirring for 10 minutes, a mixture of the 6-chloro-7-fluoropyrazolo[1,5-a]pyrimidine-5-carboxylic acid (1.00 equivalent) in THF is added. The dry-ice bath is removed after 30 minutes, and the reaction mixture is stirred for 17 hours at room temperature. The reaction mixture is treated with a 10% aqueous HCl solution, extracted with EtOAc, dried (MgSO4), and concentrated. Trituration with methylene chloride give desired product.

Workup

  1. stirringAfter vigorous stirring for 10 minutes
  2. additionis added
  3. customThe dry-ice bath is removed after 30 minutes
  4. stirringthe reaction mixture is stirred for 17 hours at room temperature
  5. additionThe reaction mixture is treated with a 10% aqueous HCl solution
  6. extractionextracted with EtOAc
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-702d74a65f334998b07306f25aa85231
Source dataset
uspto-grants-2009_08
Patent number
US07576072B2

Reaction notes

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