Pyridine → HCID 22633082, compound

HRID 2416662Notes

Reaction equation

HRID 2416662 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10](=[O:14])[C:11](Cl)=[O:12])=[N:2]1.C[C@H:16]1[NH:21][CH2:20][CH2:19][N:18]([C:22](=[O:29])[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:17]1.N1C=CC=CC=1>CC#N>[C:22]([N:18]1[CH2:19][CH2:20][N:21]([C:11](=[O:12])[C:10]([C:3]2[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[NH:1][N:2]=2)=[O:14])[CH2:16][CH2:17]1)(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 7578227(R)-1-Benzoyl-3-methylpiperazineHCID 22633105(1H-Indazol-3-yl)(oxo)acetyl chloride

Product 1

HCID 22633082HCID 22633082, compoundYield 2.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The crude residue containing (1H-Indazol-3-yl)-2-oxo-acetyl chloride (50 mg) was dissolved in dry CH3CN (7 mL), and to the resulting solution was added 3-(R)-methyl-1-benzoyl piperazine (50 mg) and pyridine (1 mL). The reaction mixture was stirred for 1 hour at room temperature then was concentrated in vacuo. The resulting residue was purified using Shimadzu automated preparative HPLC System to give 1-(benzoyl)-4-[(1H-indazol-3-yl)-2-oxoacetyl]piperazine (2.5 mg). 1H NMR (500 MHz, MeOD) δ 8.42 (m, 2H), 7.90 (m, 1H), 7.69 (m, 1H), 7.46 (m, 5H), 5.00-3.00 (m, 8H), 1.30 (m, 3H). MS m/z: (M+H)+ calcd for C21H21N4O3:377.16; found 377.28. HPLC retention time: 1.49 minutes (column A).

Workup

  1. concentrationthen was concentrated in vacuo
  2. customThe resulting residue was purified

Sources & evidence

ORD record
ord-c37d6cf427b54986a5d2ef7cd08c361c
Source dataset
uspto-grants-2004_11
Patent number
US06825201B2

Reaction notes

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