Methylamine → HCID 67097069, compound

HRID 2077045Notes

Reaction equation

HRID 2077045 reaction equation
[CH3:1][NH2:2].[C:3]1([CH:9]([C:11]2[N:12]=[C:13](OS(C(F)(F)F)(=O)=O)[C:14]3[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH2:16][C:15]=3[N:28]=2)[CH3:10])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>CC#N>[CH3:1][NH:2][C:13]1[C:14]2[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH2:16][C:15]=2[N:28]=[C:11]([CH:9]([C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)[CH3:10])[N:12]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 59312361HCID 59312361, compound

Product 1

HCID 67097069HCID 67097069, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of methylamine (2.0M, 0.65 mL, 1.30 mmol) was added to a solution of Tert-butyl 2-(1-phenylethyl)-4-{[(trifluoromethyl)sulfonyl]oxy}-5,6,8,9-tetrahydro-7H-pyrimido[4,5-d]azepine-7-carboxylate of preparation 2, step B (130 mg, 0.26 mmol) in MeCN (4.0 mL) at room temperature with stirring. The mixture was stirred at room temperature for 20 h. The solvent was evaporated in vacuo to provide the crude title compound as a yellow gum. The crude material was purified by flash column chromatography eluting with CH2Cl2:ethyl acetate (100:0 to 50:50) to yield the desired product as a white crystalline solid (89 mg, 90% yield).

Workup

  1. stirringThe mixture was stirred at room temperature for 20 h
  2. customThe solvent was evaporated in vacuo
  3. customto provide the crude title compound as a yellow gum
  4. customThe crude material was purified by flash column chromatography
  5. washeluting with CH2Cl2:ethyl acetate (100:0 to 50:50)

Sources & evidence

ORD record
ord-caa837d02d5e48c78f9db47207937a6b
Source dataset
uspto-grants-2011_04
Patent number
US07928099B2

Reaction notes

Loading…