Triethylamine → HCID 58504658, compound

HRID 2367373Notes

Reaction equation

HRID 2367373 reaction equation
[CH:1]1([NH:7][C:8]([C@H:10]2[CH2:15][CH2:14][CH2:13][NH:12][CH2:11]2)=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]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][CH:1]3[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]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 28161456HCID 28161456, compound

Product 1

HCID 58504658HCID 58504658, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

To (3S)—N-cyclohexyl-3-piperidinecarboxamide (446 mg, 2.12 mmol) in CH3CN (10 mL) was added 4,6-dichloro-2-pyrimidinamine (382 mg, 2.332 mmol) and triethylamine (0.591 mL, 4.24 mmol), and the reaction mixture was stirred overnight at 50° C. LCMS show no starting material after 3 hours. The reaction was concentrated, and 3 mL of EtOAc was added until solid dissolved. Then 15 mL of hexane was added and solid crashed out of the solution. The solid was isolated by filtration to afford the title compound (430 mg) as a white solid. LC-MS (ES) m/z=338 [M+H]+.

Workup

  1. waitLCMS show no starting material after 3 hours
  2. concentrationThe reaction was concentrated
  3. addition3 mL of EtOAc was added until solid
  4. dissolutiondissolved
  5. additionThen 15 mL of hexane was added
  6. customThe solid was isolated by filtration

Sources & evidence

ORD record
ord-95d174119af34668b69771e403acfc67
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

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