Methylamine → HCID 178453368, compound

HRID 1695096Notes

Reaction equation

HRID 1695096 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[C:7]([CH2:11][CH2:12][CH2:13][NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[NH:8]2)=[C:4]([O:22][CH2:23][C:24]2[CH:37]=[CH:36][C:27]([CH2:28][NH:29]C(=O)C(F)(F)F)=[CH:26][CH:25]=2)[N:3]=1.CN>CO>[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[C:7]([CH2:11][CH2:12][CH2:13][NH:14][C:15]([O:17][C:18]([CH3:20])([CH3:19])[CH3:21])=[O:16])[NH:8]2)=[C:4]([O:22][CH2:23][C:24]2[CH:37]=[CH:36][C:27]([CH2:28][NH2:29])=[CH:26][CH:25]=2)[N:3]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 178453369N-[4-(2-Amino-8-(3-(tert-butoxycarbonylamino)-propyl)-9H-purin-6-yloxymethyl)-benzyl]-2,2,2-trifluoro-acetamide

Product 1

HCID 178453368HCID 178453368, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

Trifluoroacetamide 11 (Example 23, 100 mg, 0.19 mmol) is dissolved in 2 mL methanol, and 2 mL methylamine (33% in ethanol) are added. The reaction mixture is stirred at 50° C. over night and all volatiles are removed in vacuo. The product is purified by flash column chromatography (CH2Cl2/MeOH 95:5 to 10:1) yielding 77 mg (0.017 mmol, 94%) of the title compound.

Workup

  1. customall volatiles are removed in vacuo
  2. customThe product is purified by flash column chromatography (CH2Cl2/MeOH 95:5 to 10:1)

Sources & evidence

ORD record
ord-1f3e8ba6dc5546c1ab60561382d327f8
Source dataset
uspto-grants-2012_04
Patent number
US08163479B2

Reaction notes

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