Triethylamine → HCID 69364884, compound

HRID 1246813Notes

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.[CH2:25]([O:27][C:28]([CH:30]1[NH:35][CH2:34][CH2:33][N:32]([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[CH2:31]1)=[O:29])[CH3:26].C(N(CC)CC)C>C(O)C>[CH2:25]([O:27][C:28]([CH:30]1[N:35]([C:2]2[N:10]=[CH:9][N:8]=[C:7]3[C:3]=2[N:4]=[C:5]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[Cl:24])[N:6]3[C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=2)[CH2:34][CH2:33][N:32]([C:36]([O:38][C:39]([CH3:40])([CH3:42])[CH3:41])=[O:37])[CH2:31]1)=[O:29])[CH3:26]

Participants

Conditions

Temperature: 60 °C

Procedure

6-Chloro-9-(4-chlorophenyl)-8-(2-chlorophenyl)-9H-purine I-(4A-7)c (103 mg, 0.27 mmol), piperazine-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester (Chiu, C. K.-F. and Griffith, D. A., EP 1004583 A2; 156 mg, 0.60 mmol), and triethylamine (95 μl, 0.68 mmol) were combined in ethanol (1.5 ml) and heated at 60° C. until complete by TLC (3 days). The reaction mixture was concentrated under reduced pressure and then purified on a Biotage™ Flash 12M column using 20 to 30% ethyl acetate in hexanes as eluant to afford title compound I-(8A-1)a (78 mg, 48%): +ESI MS (M+1) 597.3; 1H NMR (400 MHz, CD3OD) δ 8.298 (br s, 1H), 7.57 (br s, 1H), 7.48–7.25 (m, 7H), 5.60 (v br s, 1H), 4.67 (d, J=13.7 Hz, 1H), 4.23–4.05 (br m, 3H), 3.43–3.00 (br m, 2H), 1.46 (s, 9H), 1.22 (t, J=7.1 Hz, 3H).

Workup

concentrationThe reaction mixture was concentrated under reduced pressure
custompurified on a Biotage™ Flash 12M column

Sources & evidence

ORD record: ord-ea1029e404fb4b44a43f1ac32f02a15d
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07129239B2

Reaction notes

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