3-Fluorobenzylamine → HCID 58063246, compound

HRID 474327Notes

Reaction equation

HRID 474327 reaction equation
Cl[C:2]1[N:7]=[CH:6][N:5]2[N:8]=[CH:9][C:10]([C:11]([O:13][CH3:14])=[O:12])=[C:4]2[CH:3]=1.[F:15][C:16]1[CH:17]=[C:18]([CH:21]=[CH:22][CH:23]=1)[CH2:19][NH2:20].C(N(CC)C(C)C)(C)C>C(O)C>[F:15][C:16]1[CH:17]=[C:18]([CH:21]=[CH:22][CH:23]=1)[CH2:19][NH:20][C:2]1[CH:3]=[CH:4][N:5]2[N:8]=[CH:9][C:10]([C:11]([O:13][CH3:14])=[O:12])=[C:6]2[N:7]=1

Participants

5

Reactant 3

HCID 668533-FluorobenzylamineHCID 81531DiisopropylethylamineHCID 86661441HCID 86661441, compound

Product 1

HCID 58063246HCID 58063246, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of methyl 5-chloropyrazolo[1,5-c]pyrimidine-3-carboxylate (240 mg, 1.1 mM, 1.0 equiv), 3-fluorobenzylamine (200 uL, 2.0 mM, 2.0 equiv), 30 mL of ethanol and 400 uL of N,N-diisopropylethylamine (2.0 mM, 2 equiv) were combined and heated under reflux for 4 hours. The mixture was concentrated and the product collected by filtration and washed with cold ethanol to give 271 mg (80%) of methyl 5-(3-fluorobenzylamino)pyrazolo[1,5-a]pyrimidine-3-carboxylate LCMS (ESI) m+H=301.2, 1H NMR (400 MHz, DMSO-d6) δ: 8.56 (d, 1H), 8.41 (m 1H), 8.17 (s, 1H), 7.35 (m, 3H), 7.08 (td, 1H), 6.44 (d, 1H), 4.61 (d, 2H), 3.74 (s, 3H).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 4 hours
  3. concentrationThe mixture was concentrated
  4. filtrationthe product collected by filtration
  5. washwashed with cold ethanol

Sources & evidence

ORD record
ord-c5410d4f111c423bbaa644a9cdd57492
Source dataset
uspto-grants-2014_01
Patent number
US08637526B2

Reaction notes

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