Triethylamine → HCID 10347100, compound

HRID 1246817Notes

Reaction equation

HRID 1246817 reaction equation
Cl[C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[C:5]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[Cl:24])[N:6]2[C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=1.[CH:25]([N:28]1[C:32]2([CH2:37][CH2:36][NH:35][CH2:34][CH2:33]2)[C:31](=[O:38])[NH:30][CH2:29]1)([CH3:27])[CH3:26].C(N(CC)CC)C>C(O)C>[Cl:17][C:14]1[CH:13]=[CH:12][C:11]([N:6]2[C:5]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[Cl:24])=[N:4][C:3]3[C:7]2=[N:8][CH:9]=[N:10][C:2]=3[N:35]2[CH2:36][CH2:37][C:32]3([N:28]([CH:25]([CH3:26])[CH3:27])[CH2:29][NH:30][C:31]3=[O:38])[CH2:33][CH2:34]2)=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 219057796-Chloro-8-(2-chlorophenyl)-9-(4-chlorophenyl)-9H-purineHCID 219058371-(Propan-2-yl)-1,3,8-triazaspiro[4.5]decan-4-one

Product 1

HCID 10347100HCID 10347100, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 6-chloro-9-(4-chlorophenyl)-8-(2-chlorophenyl)-9H-purine I-(4A-7)c (19 mg, 0.052 mmol), 1-isopropyl-1,3,8-triazaspiro[4.5]decan-4-one (Janssen, P. A. J., U.S. Pat. No. 3,238,216; 20 mg, 0.10 mmol) and triethylamine (11 μl) in ethanol (1 ml) was stirred overnight at room temperature. The reaction mixture was concentrated under reduced pressure and then purified on a Biotage™ Flash 12S column using 3% methanol in methylene chloride as eluant to afford title compound 13A-1 (25 mg): +ESI MS (M+1) 536.3; 1H NMR (400 MHz, CD3OD) δ 8.22 (s, 1H), 7.59 (d, J=7.5 Hz, 1H), 7.46–7.35 (m, 5H), 7.29 (d, J=8.7 Hz, 2H), 4.27 (s, 2H), 4.25 (v br s, 4H), 3.15 (septuplet, J=6.6 Hz, 1H), 2.00–1.83 (m, 4H), 1.07 (d, J=6.6 Hz, 6H). A solution of the material in methylene chloride/ methanol was treated with excess 1 N HCl in diethyl ether, stirred, evaporated to dryness, and then triturated in diethyl ether to afford the hydrochloride salt of compound 13A-1 (23 mg, 77%): 1H NMR (400 MHz, CD3OD) δ 8.43 (s, 1H), 7.61 (d, J=7.5 Hz, 1H), 7.53–7.40 (m, 5H), 7.35 (d, J=8.7 Hz, 2H), 4.20 (v br s), 3.94 (septuplet, J=6.6 Hz, 1H), 2.45 (m, 4H), 1.41 (d, J=6.6 Hz, 6H).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. custompurified on a Biotage™ Flash 12S column

Sources & evidence

ORD record
ord-e59c502cfa114b1d8436866a529cc5a7
Source dataset
uspto-grants-2006_10
Patent number
US07129239B2

Reaction notes

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