Methylamine → HCID 86659195, compound

HRID 2367434Notes

Reaction equation

HRID 2367434 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](S(C)(=O)=O)[N:5]=[C:4]([N:12]2[C@H:17]([C:18]([F:21])([F:20])[F:19])[CH2:16][CH2:15][C@H:14]([C:22]([NH:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[O:23])[CH2:13]2)[CH:3]=1.C[CH2:33][N:34](C(C)C)C(C)C.CN>O1CCOCC1>[Cl:1][C:2]1[N:7]=[C:6]([NH:34][CH3:33])[N:5]=[C:4]([N:12]2[C@H:17]([C:18]([F:21])([F:20])[F:19])[CH2:16][CH2:15][C@H:14]([C:22]([NH:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[O:23])[CH2:13]2)[CH:3]=1

Participants

5

Reactant 3

HCID 6329MethylamineHCID 81531DiisopropylethylamineHCID 86659196HCID 86659196, compound

Product 1

HCID 86659195HCID 86659195, compoundYield 83.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Into a 100 mL RB flask was dissolved cis-1-[6-chloro-2-(methylsulfonyl)-4-pyrimidinyl]-N-(phenylmethyl)-6-(trifluoromethyl)-3-piperidinecarboxamide (400 mg, 0.839 mmol) in 1,4-dioxane (5 mL), then added Hunig's base (0.730 mL, 4.19 mmol), and the resulting mixture was stirred for 5 minutes. Methylamine (1.677 mL, 3.35 mmol, 2M in THF) was added, and the reaction mixture was stirred overnight at room temperature. The reaction was concentrated, and then CH3OH (15 mL) was added. An insoluble solid was observed and the mixture was filtered. The filtrate was concentrated to afford the title compound (301 mg) as a clear oil. LC-MS (ES) m/z=428 [M+H]+.

Workup

  1. concentrationThe reaction was concentrated
  2. additionCH3OH (15 mL) was added
  3. filtrationthe mixture was filtered
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-e7b29577d73048a6ae98170bcb6b9d56
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

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