Triethylamine → HCID 40011628, compound

HRID 2367372Notes

Reaction equation

HRID 2367372 reaction equation
[C:1]1([NH:7][C:8]([C@H:10]2[CH2:15][CH2:14][CH2:13][NH:12][CH2:11]2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:16][C:17]1[CH:22]=[C:21](Cl)[N:20]=[C:19]([NH2:24])[N:18]=1.C(N(CC)CC)C>CC#N>[NH2:24][C:19]1[N:20]=[C:21]([N:12]2[CH2:13][CH2:14][CH2:15][C@H:10]([C:8]([NH:7][C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[O:9])[CH2:11]2)[CH:22]=[C:17]([Cl:16])[N:18]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 655222-Amino-4,6-dichloropyrimidineHCID 9207823HCID 9207823, compound

Product 1

HCID 40011628HCID 40011628, compoundYield 65.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

To (3S)—N-phenyl-3-piperidinecarboxamide (327 mg, 1.6 mmol) in CH3CN (10 mL) was added 4,6-dichloro-2-pyrimidinamine (289 mg, 1.760 mmol) and triethylamine (0.446 mL, 3.20 mmol), and the solution was allowed to stir overnight at 50° C. The reaction was then quenched with water (2 mL), and extracted 3× with EtOAc. The organics were combined, dried (Na2SO4), filtered and concentrated to afford the crude title compound (350 mg) as a solid. LC-MS (ES) m/z=332 [M+H]+.

Workup

  1. customThe reaction was then quenched with water (2 mL)
  2. extractionextracted 3× with EtOAc
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-6b1131dc7079476eafcbb890d14ba3f7
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

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