Ethylamine → N-Cyclopropyl-5-{3-[(1-{2-[2-(ethylamino)ethoxy]phenyl}cyclopropyl)amino]-2-oxopyrazin-1(2H)-yl}-2-fluoro-4-methylbenzamide

HRID 337144Notes

Reaction equation

HRID 337144 reaction equation
[CH2:1]([NH2:3])[CH3:2].Cl[CH2:5][CH2:6][O:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]1([NH:17][C:18]2[C:19](=[O:38])[N:20]([C:24]3[C:25]([CH3:37])=[CH:26][C:27]([F:36])=[C:28]([CH:35]=3)[C:29]([NH:31][CH:32]3[CH2:34][CH2:33]3)=[O:30])[CH:21]=[CH:22][N:23]=2)[CH2:16][CH2:15]1>O1CCOCC1.C1COCC1>[CH:32]1([NH:31][C:29](=[O:30])[C:28]2[CH:35]=[C:24]([N:20]3[CH:21]=[CH:22][N:23]=[C:18]([NH:17][C:14]4([C:9]5[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=5[O:7][CH2:6][CH2:5][NH:3][CH2:1][CH3:2])[CH2:16][CH2:15]4)[C:19]3=[O:38])[C:25]([CH3:37])=[CH:26][C:27]=2[F:36])[CH2:34][CH2:33]1

Participants

5

Reactant 2

HCID 6341Ethylamine2×HCID 666892205-[3-({1-[2-(2-Chloroethoxy)phenyl]cyclopropyl}amino)-2-oxopyrazin-1(2H)-yl]-N-cyclopropyl-2-fluoro-4-methylbenzamide

Product 1

HCID 66689747N-Cyclopropyl-5-{3-[(1-{2-[2-(ethylamino)ethoxy]phenyl}cyclopropyl)amino]-2-oxopyrazin-1(2H)-yl}-2-fluoro-4-methylbenzamide

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of ethylamine (2.012 mL of 2M in THF) and 5-[3-({1-[2-(2-chloroethoxy)phenyl]cyclopropyl}amino)-2-oxopyrazin-1(2H)-yl]-N-cyclopropyl-2-fluoro-4-methylbenzamide (Example 318h, 100 mg) in dioxane (3 mL) was heated for 24 h at 100° C. in a sealed tube. Further ethylamine (2.012 mL of a 2M solution in THF) was added and the reaction was heated for a further 24 h. Purification by preparative HPLC (Xbridge column eluting with a gradient of acetonitrile in 0.2% (v/v) aqueous ammonia) gave the title compound as a solid (10 mg).

Workup

  1. temperaturethe reaction was heated for a further 24 h
  2. customPurification by preparative HPLC (Xbridge column
  3. washeluting with a gradient of acetonitrile in 0.2% (v/v) aqueous ammonia)

Sources & evidence

ORD record
ord-21065ce9ba4f44f187e8db0b773d9f02
Source dataset
uspto-grants-2014_11
Patent number
US08889692B2

Reaction notes

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