4-(2-Methylphenyl)piperidine hydrochloride → 7-Benzylamino-3-bromo-6-[4-(2-methylphenyl)piperidine-1-carbonyl]pyrazolo[1,5-a]pyrimidine

HRID 1026918Notes

Reaction equation

HRID 1026918 reaction equation
[CH2:1]([NH:8][C:9]1[N:14]2[N:15]=[CH:16][C:17]([Br:18])=[C:13]2[N:12]=[CH:11][C:10]=1[C:19]([OH:21])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[CH3:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[CH:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1>>[CH2:1]([NH:8][C:9]1[N:14]2[N:15]=[CH:16][C:17]([Br:18])=[C:13]2[N:12]=[CH:11][C:10]=1[C:19]([N:33]1[CH2:34][CH2:35][CH:30]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=2[CH3:23])[CH2:31][CH2:32]1)=[O:21])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 219369564-(2-Methylphenyl)piperidine hydrochlorideHCID 675403637-Benzylamino-3-bromopyrazolo[1,5-a]pyrimidine-6-carboxylic acid

Product 1

HCID 675403437-Benzylamino-3-bromo-6-[4-(2-methylphenyl)piperidine-1-carbonyl]pyrazolo[1,5-a]pyrimidineYield 85.5%

Procedure

In the same manner as in Example 21, step 5 and using 7-benzylamino-3-bromopyrazolo[1,5-a]pyrimidine-6-carboxylic acid (0.20 g, 0.58 mmol) obtained in Example 22, step 3 instead of 7-benzylamino-3-ethoxycarbonylpyrazolo[1,5-a]pyrimidine-6-carboxylic acid and 4-(2-methylphenyl)piperidine hydrochloride (0.15 g, 0.69 mmol), the title compound (0.25 g, 85%) was obtained.

Sources & evidence

ORD record
ord-46075d6f1bc042aab3e24dcddc53a4d9
Source dataset
uspto-grants-2014_05
Patent number
US08729264B2

Reaction notes

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