Ethyl 4-methylpiperidine-4-carboxylate hydrochloride → ethyl 1-[2-[4-(2-[3-[5-chloro-2-(difluoromethoxy)phenyl]-4-[pyrazolo[1,5-a]pyrimidine-3-amido]-1H-pyrazol-1-yl]acetyl)piperazin-1-yl]ethyl]-4-methylpiperidine-4-carboxylate formate

HRID 529801Notes

Reaction equation

HRID 529801 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:47][CH:48]([F:50])[F:49])=[C:6]([C:8]2[C:12]([NH:13][C:14]([C:16]3[CH:17]=[N:18][N:19]4[CH:24]=[CH:23][CH:22]=[N:21][C:20]=34)=[O:15])=[CH:11][N:10]([CH2:25][C:26]([N:28]3[CH2:33][CH2:32][N:31]([CH2:34][CH2:35]N4CCC([C:42]([O:44]CC)=[O:43])CC4)[CH2:30][CH2:29]3)=[O:27])[N:9]=2)[CH:7]=1.Cl.[CH3:52][C:53]1([C:59]([O:61][CH2:62][CH3:63])=[O:60])[CH2:58][CH2:57][NH:56][CH2:55][CH2:54]1>>[CH:42]([OH:44])=[O:43].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:47][CH:48]([F:50])[F:49])=[C:6]([C:8]2[C:12]([NH:13][C:14]([C:16]3[CH:17]=[N:18][N:19]4[CH:24]=[CH:23][CH:22]=[N:21][C:20]=34)=[O:15])=[CH:11][N:10]([CH2:25][C:26]([N:28]3[CH2:29][CH2:30][N:31]([CH2:34][CH2:35][N:56]4[CH2:57][CH2:58][C:53]([CH3:52])([C:59]([O:61][CH2:62][CH3:63])=[O:60])[CH2:54][CH2:55]4)[CH2:32][CH2:33]3)=[O:27])[N:9]=2)[CH:7]=1

Participants

3

Reactant 2

HCID 19361804Ethyl 4-methylpiperidine-4-carboxylate hydrochlorideHCID 118522385ethyl 1-[2-[4-(2-[3-[5-chloro-2-(difluoromethoxy)phenyl]-4-[pyrazolo[1,5-a]pyrimidine-3-amido]-1H-pyrazol-1-yl]acetyl)piperazin-1-yl]ethyl]piperidine-4-carboxylate

Product 1

HCID 118523185ethyl 1-[2-[4-(2-[3-[5-chloro-2-(difluoromethoxy)phenyl]-4-[pyrazolo[1,5-a]pyrimidine-3-amido]-1H-pyrazol-1-yl]acetyl)piperazin-1-yl]ethyl]-4-methylpiperidine-4-carboxylate formate

Procedure

Using synthetic method analoguous to that of ethyl 1-[2-[4-(2-[3-[5-chloro-2-(difluoromethoxy)phenyl]-4-[pyrazolo[1,5-a]pyrimidine-3-amido]-1H-pyrazol-1-yl]acetyl)piperazin-1-yl]ethyl]piperidine-4-carboxylate, the title compound was prepared from ethyl 4-methylpiperidine-4-carboxylate hydrochloride. LCMS (Method 24) [M+H]+=728.2, RT=1.87 min. 1H NMR (400 MHz, DMSO-d6) δ: (ppm) 9.75 (s, 1H), 9.34 (dd, 1H, J=1.2, 6.8 Hz), 8.69-8.68 (m, 2H), 8.30 (s, 1H), 7.62 (dd, 1H, J=2.8, 8.8 Hz), 7.55 (d, 1H, J=2.8 Hz), 7.46 (d, 1H, J=8.8 Hz), 7.28 (dd, 1H, J=4.4, 6.8 Hz), 7.08 (t, 1H, J=73.2 Hz), 5.22 (s, 2H), 4.06 (q, 2H, J=7.2 Hz), 2.67-2.60 (m, 2H), 2.44-2.38 (m, 8H), 2.09-2.04 (m, 2H), 1.97-1.93 (m, 2H), 1.42-1.41 (m, 2H), 1.16 (t, 3H, J=7.2 Hz), 1.10 (s, 3H).

Sources & evidence

ORD record
ord-4228969b10e74759b628a41a3ad176b7
Source dataset
uspto-grants-2016_05
Patent number
US09346815B2

Reaction notes

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