Triethylamine → HCID 10163568, compound

HRID 584567Notes

Reaction equation

HRID 584567 reaction equation
[NH2:1][CH:2]1[CH:7]2[CH:3]1[CH2:4][N:5]([C:8]1[N:32]=[CH:31][C:11]3[N:12]=[CH:13][N:14]=[C:15]([NH:16][C:17]4[CH:22]=[CH:21][C:20]([O:23][C:24]5[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=5)=[C:19]([CH3:30])[CH:18]=4)[C:10]=3[CH:9]=1)[CH2:6]2.C(N(CC)CC)C.[CH:40]1([C:43](Cl)=[O:44])[CH2:42][CH2:41]1>C(Cl)Cl.C(Cl)(Cl)Cl>[CH3:30][C:19]1[CH:18]=[C:17]([NH:16][C:15]2[C:10]3[CH:9]=[C:8]([N:5]4[CH2:4][CH:3]5[CH:7]([CH:2]5[NH:1][C:43]([CH:40]5[CH2:42][CH2:41]5)=[O:44])[CH2:6]4)[N:32]=[CH:31][C:11]=3[N:12]=[CH:13][N:14]=2)[CH:22]=[CH:21][C:20]=1[O:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 77637Cyclopropanecarbonyl chlorideHCID 10113118HCID 10113118, compound

Product 1

HCID 10163568HCID 10163568, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 107.4 mg (0.25 mmol) of [6-(6-amino-3-aza-bicyclo[3.1.0]hex-3-yl)-pyrido[3,4-d]pyrimidin-4-yl]-(3-methyl-4-phenoxy-phenyl)-amine and 35.2 μL (0.25 mmol) of triethylamine in 0.5 mL of methylene chloride in an ice/brine bath was treated with 24.1 μL of cyclopropanecarbonyl chloride. The reaction was allowed to warm to room temperature and stirred for 1 hour. The mixture was diluted with chloroform and washed with 2×50 mL of saturated sodium bicarbonate. The organics were dried over sodium sulfate, filtered and concentrated under vacuum. The residue was recrystallized from ethyl acetate to afford 91.7 mg (73%) of the title compound. 1H NMR (CDCl3): δ 8.78 (s, 1), 8.37 (s, 1), 7.63 (m, 1), 7.53 (m, 1), 7.26 (m, 2), 6.95 (m, 1), 6.89 (m, 3), 6.79 (s, 1), 3.87 (d, 2), 3.48 (m, 2), 2.38 (m, 1), 2.21 (s, 3), 184 (m, 2), 1.33 (m, 1), 0.89 (m, 2), 0.72 (m, 2). M.S. (m+1): 493; HPLC retention time (minutes): 6.672.

Workup

  1. washwashed with 2×50 mL of saturated sodium bicarbonate
  2. dry with materialThe organics were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum
  5. customThe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-9bf9b27f47e84c7bb9621939da56f738
Source dataset
uspto-grants-2005_08
Patent number
US06927220B2

Reaction notes

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