Methylamine → HCID 58989135, compound

HRID 1695088Notes

Reaction equation

HRID 1695088 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH2:11][CH2:12][CH2:13][N:14]=[N+:15]=[N-:16])=[C:4]([O:17][CH2:18][C:19]2[CH:32]=[CH:31][C:22]([CH2:23][NH:24]C(=O)C(F)(F)F)=[CH:21][CH:20]=2)[N:3]=1.CN>CO>[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH2:11][CH2:12][CH2:13][N:14]=[N+:15]=[N-:16])=[C:4]([O:17][CH2:18][C:19]2[CH:20]=[CH:21][C:22]([CH2:23][NH2:24])=[CH:31][CH:32]=2)[N:3]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 58989129N-[4-(2-Amino-9-(3-azidopropyl)-purine-6-yloxymethyl)-benzyl]-2,2,2-trifluoro-acetamide

Product 1

HCID 58989135HCID 58989135, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

Azide 23 (Example 10, 50 mg, 0.11 mmol) is dissolved in 1 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 10:1) to yield 33.5 mg. 1H-NMR (400 MHz, DMSO-d6): δ=7.85 (s, 1H, H-8), 7.41, (d, J=8.1, 2H, ArH), 7.35 (d, J=8.1, 2H, ArH), 6.44 (s br, 2H, NH2), 5.44 (s, 2H, OCH2), 4.05 (t, J=, 2H, CH2), 3.72 (s, 2H, CH2), 3.35 (t, J=6.5, 2H, CH2), 1.99 (m, 2H, CH2) ppm. MS (ESI) m/z 354.1 [M+H]+.

Workup

  1. customall volatiles are removed in vacuo
  2. customThe product is purified by flash column chromatography (CH2Cl2/MeOH 10:1)
  3. customto yield 33.5 mg

Sources & evidence

ORD record
ord-7f2c2b50da684c1d844a3506ee837d33
Source dataset
uspto-grants-2012_04
Patent number
US08163479B2

Reaction notes

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