Ethylamine → HCID 59639590, compound

HRID 556636Notes

Reaction equation

HRID 556636 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[N:9]1[C:14]2[N:15]=[C:16]([NH:27][CH2:28][C:29]([OH:31])=O)[N:17]=[C:18]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:20]=3[CH3:26])[C:13]=2[CH:12]=[CH:11][C:10]1=[O:32].C[N:34]1CCO[CH2:36][CH2:35]1.CN1CCCC1=O.Cl.CN(C)CCCN=C=NCC.C(N)C>CCOC(C)=O>[F:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[C:3]=1[N:9]1[C:14]2[N:15]=[C:16]([NH:27][CH2:28][C:29]([NH:34][CH2:35][CH3:36])=[O:31])[N:17]=[C:18]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:20]=3[CH3:26])[C:13]=2[CH:12]=[CH:11][C:10]1=[O:32]

Participants

7

Reactant 5

HCID 6341EthylamineHCID 79724-MethylmorpholineHCID 13387N-methyl-2-pyrrolidoneHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 59639631HCID 59639631, compound

Product 1

HCID 59639590HCID 59639590, compoundYield 68.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The product of Example 191 (50 mg, 0.11 mmol), n-hydroxybenzotriazole (21 mg, 0.34 mmol), 1-methylmorpholine (19 uL, 0.172 mmol), N-methylpyrrolidinone (2.5 mmol) were dissolved together, then 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (66 mg, 0.34 mmol) was added, stirred 1 h, and then ethylamine (2 M in THF) (1.0 mL, 2.0 mmol) was added and the reaction was stirred at 23° for 16 h, diluted with EtOAc (50 mL), and washed with 10% aq citric acid (2×20 mL), H2O (20 mL), and satd aq NaCl (20 mL), dried (MgSO4) concentrated and purified by chromatotron chromatography (CH2Cl2/CH3OH) to afford 35 mg of the title compound 2-[[8-(2,6-difluorophenyl)-4-(4-fluoro-2-methylphenyl)-7,8-dihydro-7-oxopyrido[2,3-d]pyrimidin-2-yl]amino]-N-ethylacetamide as a white powder. mp=250-253 (dee). LC MS (m/e)=468.2 (MH+). Rt=1.87 min.

Workup

  1. stirringthe reaction was stirred at 23° for 16 h
  2. washwashed with 10% aq citric acid (2×20 mL), H2O (20 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. custompurified by chromatotron chromatography (CH2Cl2/CH3OH)

Sources & evidence

ORD record
ord-707abaa72be44bf8ab1d8080c1c70c7d
Source dataset
uspto-grants-2011_11
Patent number
US08058282B2

Reaction notes

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