Methanol → HCID 58721700, compound

HRID 1246822Notes

Reaction equation

HRID 1246822 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[Cl:23])=[N:15][C:14]3[C:9]2=[N:10][CH:11]=[N:12][C:13]=3[N:24]2[CH2:29][CH2:28][C:27]([NH:33][CH3:34])([C:30](N)=[O:31])[CH2:26][CH2:25]2)=[CH:4][CH:3]=1.[CH3:35][OH:36]>>[CH3:35][O:36][C:30]([C:27]1([NH:33][CH3:34])[CH2:28][CH2:29][N:24]([C:13]2[N:12]=[CH:11][N:10]=[C:9]3[C:14]=2[N:15]=[C:16]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[Cl:23])[N:8]3[C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)[CH2:25][CH2:26]1)=[O:31]

Participants

3

Reactant 2

HCID 887MethanolHCID 86592222HCID 86592222, compound

Product 1

HCID 58721700HCID 58721700, compound

Conditions

Temperature
60 °C

Procedure

1-[9-(4-Chlorophenyl)-8-(2-chlorophenyl)-9H-purin-6-yl]-4-methylaminopiperidine-4-carboxylic acid amide 7A-87 (Example 164; 53 mg, 0.093 mmol) and Amberlyst 15 (0.8 g) in methanol (5 ml) was sealed in a tube and then heated to 60° C. for 20 h. The resin was removed by filtration and washed with 2:1 methanol/triethylamine and then 10% NH4OH in methanol. The combined organic layers were concentrated and then purified on a Biotage™ Flash 12S column using 0–2–4% methanol in methylene chloride as eluant to give title compound 21A-1 as a light brown solid (26 mg, 55%): +ESI MS (M+1) 511.1; 1H NMR (400 MHz, CD2Cl2) δ 8.28 (s, 1H), 7.52 (d, J=8.3 Hz, 1H), 7.44–7.32 (m, 5H), 7.21 (d, J=8.7 Hz, 2H), 5.55 (v br s, 1H), 4.65 (v br s, 2H), 4.13 (v br s, 2H), 3.71 (s, 3H), 2.28 (s, 3H), 2.07 (ddd, J=13.7, 9.6, 3.7 Hz, 2H), 1.79 (dt, J=13.7, 3.9 Hz, 2H).

Workup

  1. customThe resin was removed by filtration
  2. washwashed with 2:1 methanol/triethylamine
  3. concentrationThe combined organic layers were concentrated
  4. custompurified on a Biotage™ Flash 12S column

Sources & evidence

ORD record
ord-07c4788d57a54c55828b429f6591808d
Source dataset
uspto-grants-2006_10
Patent number
US07129239B2

Reaction notes

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