Triethylamine → 1-(9-(4-chlorophenyl)-8-(2-chlorophenyl)-9H-purin-6-yl)-4-ethylaminopiperidine-4-carboxylic acid amide

HRID 1246821Notes

Reaction equation

HRID 1246821 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.C(N(CC)CC)C.[CH2:32]([NH:34][C:35]1([C:41]([NH2:43])=[O:42])[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]1)[CH3:33]>CC(C)=O.O>[Cl:17][C:14]1[CH:15]=[CH:16][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:38]2[CH2:37][CH2:36][C:35]([NH:34][CH2:32][CH3:33])([C:41]([NH2:43])=[O:42])[CH2:40][CH2:39]2)=[CH:12][CH:13]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 965734-(Ethylamino)piperidine-4-carboxamideHCID 219057796-Chloro-8-(2-chlorophenyl)-9-(4-chlorophenyl)-9H-purine

Product 1

HCID 100520401-(9-(4-chlorophenyl)-8-(2-chlorophenyl)-9H-purin-6-yl)-4-ethylaminopiperidine-4-carboxylic acid amide

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent2×

Procedure

To a pale orange solution of 6-chloro-9-(4-chlorophenyl)-8-(2-chlorophenyl)-9H-purine I-(4A-7)c (1.00 g, 2.66 mmol) in acetone (13 ml) at room temperature was added triethylamine (410 μl, 2.94 mmol). A solution of 4-ethylamino-piperidine-4-carboxylic acid amide I-(7A-80)f in water (1.5 ml) was then added to give a clear yellow reaction solution. After stirring at room temperature for 3 days the cloudy white reaction mixture was diluted with water (11 ml). After stirring 1 hour at room temperature followed by 1 hour at 0° C., the precipitate was collected on a sintered glass funnel and rinsed with cold 1:1, acetone: H2O. The solid was dried, in vacuo, to give title compound 20A-1 as a colorless solid (1.22 g, 90%): +ESI MS (M+1) 510.2; 1H NMR (400 MHz, CD3OD) δ 8.19 (s, 1H), 7.57 (d, J=7.0 Hz,1H), 7.45–7.35 (m, 5H), 7.26 (d, J=8.7 Hz, 2H), 4.54 (br s, 2H), 4.24 (br s, 2H), 2.51 (q, J=7.0 Hz, 2H), 2.12–2.06 (m, 2H), 1.76–1.72 (m, 2H) 1.10 (t, J=7.0 Hz, 3H).

Workup

  1. customto give a clear yellow reaction solution
  2. stirringAfter stirring 1 hour at room temperature
  3. waitfollowed by 1 hour at 0° C.
  4. customthe precipitate was collected on a sintered glass funnel
  5. washrinsed with cold 1:1, acetone
  6. customThe solid was dried, in vacuo

Sources & evidence

ORD record
ord-89b0f79bae9d4715ba0b68e89bee426e
Source dataset
uspto-grants-2006_10
Patent number
US07129239B2

Reaction notes

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