Water → HCID 58728949, compound

HRID 551875Notes

Reaction equation

HRID 551875 reaction equation
[C:1]([C:5]1[CH:42]=[CH:41][C:8]([C:9]([NH:11][C:12]2[C:13]([CH3:40])=[C:14]([C:18]3[N:23]=[C:22]([NH:24][C:25]4[CH:30]=[CH:29][C:28]([CH2:31][CH2:32]OS(C)(=O)=O)=[CH:27][CH:26]=4)[C:21](=[O:38])[N:20]([CH3:39])[CH:19]=3)[CH:15]=[CH:16][CH:17]=2)=[O:10])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[NH2:43][CH:44]1[CH2:49][CH2:48][O:47][CH2:46][CH2:45]1.O>C(#N)C>[C:1]([C:5]1[CH:42]=[CH:41][C:8]([C:9]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]3[N:23]=[C:22]([NH:24][C:25]4[CH:30]=[CH:29][C:28]([CH2:31][CH2:32][NH:43][CH:44]5[CH2:49][CH2:48][O:47][CH2:46][CH2:45]5)=[CH:27][CH:26]=4)[C:21](=[O:38])[N:20]([CH3:39])[CH:19]=3)[C:13]=2[CH3:40])=[O:10])=[CH:7][CH:6]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 962WaterHCID 4192234-AminotetrahydropyranHCID 86608448HCID 86608448, compound

Product 1

HCID 58728949HCID 58728949, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
90 °C

Procedure

Methanesulfonic acid 2-(4-{6-[3-(4-tert-butyl-benzoylamino)-2-methyl-phenyl]-4-methyl-3-oxo-3,4-dihydro-pyrazin-2-ylamino}-phenyl)-ethyl ester (3) (0.2 g; 0.34 mmol) was dissolved in acetonitrile (2 mL) and excess 4-aminotetrahydropyran (0.25 mL) was added. The reaction vessel was sealed and heated to 90° C. for 4 hr. Water (10 mL) was added to the reaction vessel and the reaction was extracted with EtOAc (3×25 mL). The EtOAc layers were pooled, washed with brine, dried over solid sodium sulfate and filtered. The filtrate was then adsorbed directly onto silica and chromatographed using methanol/CH2Cl2 (1:9) as eluent to provide 75 mg of 4-tert-butyl-N-[2-methyl-3-(4-methyl-5-oxo-6-{4-[2-(tetrahydro-pyran-4-ylamino)-ethyl]-phenylamino}-4,5-dihydro-pyrazin-2-yl)-phenyl]-benzamide (4) as a light tan solid. MS 594.33 (M+H).

Workup

  1. customThe reaction vessel was sealed
  2. extractionthe reaction was extracted with EtOAc (3×25 mL)
  3. washwashed with brine
  4. dry with materialdried over solid sodium sulfate
  5. filtrationfiltered
  6. customchromatographed

Sources & evidence

ORD record
ord-ff97ed52ee09471f95ce6f1d8cf3e7a5
Source dataset
uspto-grants-2011_05
Patent number
US07947835B2

Reaction notes

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