1-Ethylpiperazine → Pyrazolo[1,5-a]pyrimidine-3-carboxylic acid {3-(5-chloro-2-difluoromethoxy-phenyl)-1-[2-(4-ethyl-piperazin-1-yl)-2-oxo-ethyl]-1H-pyrazol-4-yl}-amide

HRID 529776Notes

Reaction equation

HRID 529776 reaction equation
ClC1C=CC(OC(F)F)=C(C2C(NC(C3C=NN4C=CC=NC=34)=O)=C[N:10]([CH2:25][C:26]([N:28]3[CH2:35][C@@H:34]4[C@@H:30](CN(C)C4)[CH2:29]3)=O)N=2)C=1.[Cl:41][C:42]1[CH:43]=[CH:44][C:45]([O:69][CH:70]([F:72])[F:71])=[C:46]([C:48]2[C:52]([NH:53][C:54]([C:56]3[CH:57]=[N:58][N:59]4[CH:64]=[CH:63][CH:62]=[N:61][C:60]=34)=[O:55])=[CH:51][N:50]([CH2:65][C:66](O)=[O:67])[N:49]=2)[CH:47]=1.C(N1CCNCC1)C>>[Cl:41][C:42]1[CH:43]=[CH:44][C:45]([O:69][CH:70]([F:71])[F:72])=[C:46]([C:48]2[C:52]([NH:53][C:54]([C:56]3[CH:57]=[N:58][N:59]4[CH:64]=[CH:63][CH:62]=[N:61][C:60]=34)=[O:55])=[CH:51][N:50]([CH2:65][C:66]([N:10]3[CH2:25][CH2:26][N:28]([CH2:29][CH3:30])[CH2:35][CH2:34]3)=[O:67])[N:49]=2)[CH:47]=1

Participants

4

Reactant 3

HCID 791961-EthylpiperazineHCID 118522370{3-(5-Chloro-2-difluoromethoxy-phenyl)-4-[(pyrazolo[1,5-a]pyrimidine-3-carbonyl)amino]pyrazol-1-yl}acetic acidHCID 118522535Cis-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid {3-(5-chloro-2-difluoromethoxyphenyl)1-[2-(5-methylhexahydropyrrolo[3,4-c]pyrrol-2-yl)-2-oxoethyl]-1H-pyrazol-4-yl}amide

Product 1

HCID 118523275Pyrazolo[1,5-a]pyrimidine-3-carboxylic acid {3-(5-chloro-2-difluoromethoxy-phenyl)-1-[2-(4-ethyl-piperazin-1-yl)-2-oxo-ethyl]-1H-pyrazol-4-yl}-amide

Procedure

The title compound was prepared in an analogous manner to cis-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid {3-(5-chloro-2-difluoromethoxyphenyl)1-[2-(5-methylhexahydropyrrolo[3,4-c]pyrrol-2-yl)-2-oxoethyl]-1H-pyrazol-4-yl}amide using {3-(5-chloro-2-difluoromethoxy-phenyl)-4-[(pyrazolo[1,5-a]pyrimidine-3-carbonyl)amino]pyrazol-1-yl}acetic acid and ethyl piperazine to afford the title compound as a white solid. LCMS (Method 5) [M+H]+=559.1, RT=2.89 min. 1H NMR (400 MHz, DMSO-d6) δ: (ppm) 9.75 (s, 1H), 9.34 (dd, 1H, J=1.6, 7.0 Hz), 8.69-8.67 (m, 2H), 8.31 (s, 1H), 7.63 (dd, 1H, J=2.7, 8.8 Hz), 7.56 (d, 1H, J=2.6 Hz), 7.46 (d, 1H, J=9.0 Hz), 7.29 (dd, 1H, J=4.2, 7.1 Hz), 7.25 (t, 1H, J=73.5 Hz), 5.23 (s, 2H), 3.50-3.49 (m, 4H), 2.41-2.32 (m, 6H), 1.02 (t, 3H, J=7.1 Hz).

Sources & evidence

ORD record
ord-8889acea2ee84474af1bab59a25ffce8
Source dataset
uspto-grants-2016_05
Patent number
US09346815B2

Reaction notes

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