Dimethylformamide → HCID 11719402, compound

HRID 1351118Notes

Reaction equation

HRID 1351118 reaction equation
[OH:1][C@@:2]1([C:9]#[C:10][C:11]2[N:19]=[C:18]3[C:14]([NH:15][CH:16]=[N:17]3)=[C:13]([NH:20][CH:21]([CH2:24][CH3:25])[CH2:22][CH3:23])[N:12]=2)[CH2:7][CH2:6][CH2:5][C@@H:4]([CH3:8])[CH2:3]1.Cl.ClC[C:29]1[N:30]=[C:31]([CH3:34])[S:32][CH:33]=1.[CH3:35]N(C=O)C>>[OH:1][C@@:2]1([C:9]#[C:10][C:11]2[N:19]=[C:18]3[C:14]([N:15]=[CH:16][N:17]3[CH2:35][C:33]3[S:32][C:31]([CH3:34])=[N:30][CH:29]=3)=[C:13]([NH:20][CH:21]([CH2:22][CH3:23])[CH2:24][CH3:25])[N:12]=2)[CH2:7][CH2:6][CH2:5][C@@H:4]([CH3:8])[CH2:3]1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 27342034-(Chloromethyl)-2-methyl-1,3-thiazole--hydrogen chloride (1/1)HCID 21097916HCID 21097916, compound

Product 1

HCID 11719402HCID 11719402, compound

Procedure

2-{2-[1-(S)-Hydroxy-3(R)-methyl-1-cyclohexyl]ethyn-1-yl}-N6-(3-pentyl)adenine (56 mg, 0.1640 mmol) and 4-chloromethyl-2-methylthiazole hydrochloride (127 mg, 0.6899 mmol) were stirred in DMF (8 mL) at 150° C. for 22 h. The reaction mixture was adhered to silica and purified by column chromatography, eluting with a gradient of DCM/MeOH (0–6%) to afford pure 31 as an off white solid: yield 2 mg, 3%. 1H NMR (CD3OD) δ 8.12 (s, 1H), 7.29 (s, 1H), 5.44 (s, 2H), 4.22 (m, 1H), 2.65 (s, 3H), 2.14–2.05, 1.94–1.37, 0.99–0.80 (3×m, 21H), 1.18 (t, 1H, J=12.2 Hz). LRMS ESI (M+H+) 453.2.

Workup

  1. custompurified by column chromatography
  2. washeluting with a gradient of DCM/MeOH (0–6%)
  3. customto afford pure 31 as an off white solid

Sources & evidence

ORD record
ord-6d34717186c94d198b6b1273dc02a09d
Source dataset
uspto-grants-2007_05
Patent number
US07217702B2

Reaction notes

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