4-(4-Fluorophenyl)-1,2,3,6-tetrahydropyridine hydrochloride → 7-(2,5-Dimethylphenylamino)-3-ethoxycarbonyl-6-[4-(4-fluorophenyl)-1,2,3,6-tetrahydropyridine-1-carbonyl]pyrazolo[1,5-a]pyrimidine

HRID 1027043Notes

Reaction equation

HRID 1027043 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[NH:9][C:10]1[N:15]2[N:16]=[CH:17][C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[C:14]2[N:13]=[CH:12][C:11]=1[C:24]([OH:26])=O.Cl.[F:28][C:29]1[CH:34]=[CH:33][C:32]([C:35]2[CH2:36][CH2:37][NH:38][CH2:39][CH:40]=2)=[CH:31][CH:30]=1>>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[NH:9][C:10]1[N:15]2[N:16]=[CH:17][C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[C:14]2[N:13]=[CH:12][C:11]=1[C:24]([N:38]1[CH2:37][CH:36]=[C:35]([C:32]2[CH:33]=[CH:34][C:29]([F:28])=[CH:30][CH:31]=2)[CH2:40][CH2:39]1)=[O:26]

Participants

3

Reactant 2

HCID 1977474-(4-Fluorophenyl)-1,2,3,6-tetrahydropyridine hydrochlorideHCID 675407397-(2,5-Dimethylphenylamino)-3-ethoxycarbonylpyrazolo[1,5-a]pyrimidine-6-carboxylic acid

Product 1

HCID 675408077-(2,5-Dimethylphenylamino)-3-ethoxycarbonyl-6-[4-(4-fluorophenyl)-1,2,3,6-tetrahydropyridine-1-carbonyl]pyrazolo[1,5-a]pyrimidineYield 75%

Procedure

In the same manner as in Example 21, step 5 and using 7-(2,5-dimethylphenylamino)-3-ethoxycarbonylpyrazolo[1,5-a]pyrimidine-6-carboxylic acid (110 mg, 0.31 mmol) obtained in Example 88, step 2 and 4-(4-fluorophenyl)-1,2,3,6-tetrahydropyridine hydrochloride (79 mg, 0.37 mmol), the title compound (119 mg, 75%) was obtained.

Sources & evidence

ORD record
ord-d6689159ee5d41b1ab7063f0db2d40dd
Source dataset
uspto-grants-2014_05
Patent number
US08729264B2

Reaction notes

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