Diisopropylethylamine → HCID 10369984, compound

HRID 348029Notes

Reaction equation

HRID 348029 reaction equation
Cl[C:2]1[N:7]2[N:8]=[C:9]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[Cl:24])[C:10]([C:11]3[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=3)=[C:6]2[N:5]=[C:4]([CH3:25])[CH:3]=1.CCN(C(C)C)C(C)C.[C:35]([O:39][C:40]([N:42]1[CH2:47][CH2:46][NH:45][CH2:44][CH2:43]1)=[O:41])([CH3:38])([CH3:37])[CH3:36]>ClCCCl>[C:35]([O:39][C:40]([N:42]1[CH2:47][CH2:46][N:45]([C:2]2[N:7]3[N:8]=[C:9]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=4[Cl:24])[C:10]([C:11]4[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=4)=[C:6]3[N:5]=[C:4]([CH3:25])[CH:3]=2)[CH2:44][CH2:43]1)=[O:41])([CH3:38])([CH3:36])[CH3:37]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 210837217-Chloro-3-(4-chlorophenyl)-2-(2-chlorophenyl)-5-methylpyrazolo[1,5-a]pyrimidine

Product 1

HCID 10369984HCID 10369984, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 7-chloro-3-(4-chlorophenyl)-2-(2-chlorophenyl)-5-methylpyrazolo[1,5-a]pyrimidine (I-3A-4b; 109 mg, 0.280 mmol) and Argonaut™ PS-DIEA (97 mg, 0.38 mmol) in 1,2-dichloroethane (2.8 ml) was added piperazine-1-carboxylic acid tert-butyl ester (70.5 mg, 0.378 mmol). The mixture was stirred at room temperature for 19 hours, filtered, concentrated and then purified on a Biotage™ Flash 12M column using 0–35% ethyl acetate in hexanes as eluant to afford, after trituration from hexanes/methylene chloride, product 5A-1 (132 mg, 88%) as an off-white solid: +ESI MS (M+1) 538.4; 1H NMR (400 MHz, CD2Cl2) δ 7.48–7.32 (m, 6H), 7.22 (d, J=8.7 Hz, 2H), 6.13 (s, 1H), 3.73–3.61 (m, 8H), 2.56 (s, 3H), 1.45 (s, 9H).

Workup

  1. filtrationfiltered
  2. concentrationconcentrated
  3. custompurified on a Biotage™ Flash 12M column
  4. customto afford

Sources & evidence

ORD record
ord-44838797454942a8ac1bd2448a69712d
Source dataset
uspto-grants-2007_02
Patent number
US07176210B2

Reaction notes

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