Triethylamine → HCID 68158055, compound

HRID 243452Notes

Reaction equation

HRID 243452 reaction equation
Cl.[F:2][C:3]1[CH:4]=[CH:5][C:6]2[N:10]=[C:9]([CH2:11][NH2:12])[N:8]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:7]=2[CH:19]=1.[NH2:20][C:21]1[C:26]([C:27]#[N:28])=[C:25](Cl)[N:24]=[CH:23][N:22]=1.C(N(CC)CC)C>C(O)(C)C>[NH2:20][C:21]1[C:26]([C:27]#[N:28])=[C:25]([NH:12][CH2:11][C:9]2[N:8]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:7]3[CH:19]=[C:3]([F:2])[CH:4]=[CH:5][C:6]=3[N:10]=2)[N:24]=[CH:23][N:22]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 122782624-Amino-6-chloropyrimidine-5-carbonitrileHCID 68157878HCID 68157878, compound

Product 1

HCID 68158055HCID 68158055, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

(6-Fluoro-1-phenyl-1H-benzoimidazol-2-yl)methylamine hydrochloride (0.113 g, 0.4 mmol), 4-amino-6-chloropyrimidine-5-carbonitrile (0.123 g, 0.8 mmol), triethylamine (0.28 mL, 2 mmol) in isopropanol (2 mL) was heated to 80° C. in a sealed tube for 2 h. After cooling the pink solid was removed by filtration and washed with isopropanol (0.5 mL). This material was purified by column chromatography (Si—PCC, gradient 0-4% MeOH in DCM). Product containing fractions were evaporated to a white solid. This was triturated with diethyl ether and dried to give 371 as a white solid, (70 mg, 69%). LCMS (Method C): RT 3.54 min [M+H]+ 360.02. 1H NMR δ (ppm) (DMSO-d): 7.87 (1H, s), 7.69 (1H, t, J=5.2 Hz), 7.65 (1H, dd, J=8.80, 4.87 Hz), 7.64-7.46 (5H, m), 7.22 (2H, s), 7.06 (1H, ddd, J=9.86, 8.79, 2.53 Hz), 6.87 (1H, dd, J=8.97, 2.51 Hz), 4.62 (2H, d, J=5.37 Hz)

Workup

  1. temperatureAfter cooling the pink solid
  2. customwas removed by filtration
  3. washwashed with isopropanol (0.5 mL)
  4. customThis material was purified by column chromatography (Si—PCC, gradient 0-4% MeOH in DCM)
  5. additionProduct containing fractions
  6. customwere evaporated to a white solid
  7. customThis was triturated with diethyl ether
  8. customdried

Sources & evidence

ORD record
ord-f90868f319804bceb09807d247a7628f
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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