Acetyl chloride → HCID 10028110, compound

HRID 348030Notes

Reaction equation

HRID 348030 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:10]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[Cl:31])=[N:11][N:12]3[C:17]([N:18]4[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]4)=[CH:16][C:15]([CH3:24])=[N:14][C:13]=23)=[CH:5][CH:4]=1.CCN(C(C)C)C(C)C.[C:41](Cl)(=[O:43])[CH3:42]>C(Cl)Cl>[Cl:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[C:10]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[Cl:31])=[N:11][N:12]3[C:17]([N:18]4[CH2:19][CH2:20][N:21]([C:41](=[O:43])[CH3:42])[CH2:22][CH2:23]4)=[CH:16][C:15]([CH3:24])=[N:14][C:13]=23)=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 81531Diisopropylethylamine2×HCID 131726250HCID 131726250, compound

Product 1

HCID 10028110HCID 10028110, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 3-(4-chlorophenyl)-2-(2-chlorophenyl)-5-methyl-7-piperazin-1-yl-pyrazolo[1,5-a]pyrimidine, hydrochloride salt (6A-3; 25 mg, 0.049 mmol), Argonaut™ PS-DIEA (63 mg, 0.24 mmol) and diisopropylethylamine (0.020 ml, 0.11 mmol) in methylene chloride (1 ml), was added acetyl chloride (0.005 ml, 0.074 mmol). After stirring 20 minutes, the reaction was filtered, concentrated and then purified on a Biotage™ Flash 12S column using 0–50% ethyl acetate in hexanes as eluant to afford, after trituration from hexanes/methylene chloride, 7A-1 (19 mg, 79%) as a solid: +ESI MS (M+1) 480.3; 1H NMR (400 MHz, CD3OD) δ 7.49–7.34 (m, 6H), 7.23 (d, J=8.7 Hz, 2H), 6.14 (s, 1H), 3.84–3.78 (m, 4H), 3.71–3.61 (m, 4H), 2.57 (s, 3H), 2.10 (s, 3H).

Workup

  1. filtrationthe reaction was filtered
  2. concentrationconcentrated
  3. custompurified on a Biotage™ Flash 12S column
  4. customto afford

Sources & evidence

ORD record
ord-7b9fa5029b974e128e969b1e5d4dcdaf
Source dataset
uspto-grants-2007_02
Patent number
US07176210B2

Reaction notes

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