Morpholine → HCID 178422829, compound
Reaction equation
N1C(C(O)=O)=CC(C(O)=O)=N1.[C:12]([C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:24]=[CH:23][N:22]([CH2:25][C@H:26]([NH:28][C:29]([C:31]3[NH:35][N:34]=[C:33]([C:36]([OH:38])=O)[CH:32]=3)=[O:30])[CH3:27])[N:21]=2)=[CH:16][C:15]=1[CH3:39])#[N:13].[NH:40]1[CH2:45][CH2:44][O:43][CH2:42][CH2:41]1.ClC1C=C(C2OC(CCNC(C3NN=C(C(N4CCNCC4)=O)C=3)=O)=CC=2)C=CC=1Cl>>[C:12]([C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:24]=[CH:23][N:22]([CH2:25][C@H:26]([NH:28][C:29]([C:31]3[NH:35][N:34]=[C:33]([C:36]([N:40]4[CH2:45][CH2:44][O:43][CH2:42][CH2:41]4)=[O:38])[CH:32]=3)=[O:30])[CH3:27])[N:21]=2)=[CH:16][C:15]=1[CH3:39])#[N:13]Participants
Procedure
The title compound was synthesized using the method of Example 30, but replacing 5-pyridin-4-yl-4H-pyrazole-3-carboxylic acid with 3,5-pyrazoledicarboxylic acid. Thus obtained (R)-5-(1-(3-(4-cyano-3-methylphenyl)-1H-pyrazol-1-yl)propan-2-ylcarbamoyl)-1H-pyrazole-3-carboxylic acid was coupled with morpholine according to synthesis of 5-(piperazine-1-carbonyl)-2H-pyrazole-3-carboxylic acid {2-[5-(3,4-dichlorophenyl)furan-2-yl]ethyl}amide, Example 1, but replacing piperazine with morpholine. Crude product was purified by chromatography (CombiFlash, 1st column silica, eluent: 0-10% MeOH/DCM; 2nd column C-18 RP eluent: 0-100% MeCN/water) to obtain 24 mg (45%) of the title compound. 1H-NMR (400 MHz; CDCl3): δ 1.25 (d, 3H), 2.60 (s, 3H), 3.79 (m, 8H), 4.29 (dd, 1H), 4.42 (dd, 1H), 4.60 (m, 1H), 6.61 (d, 1H), 7.02 (s, 1H), 7.47 (d, 1H), 7.63 (m, 2H), 7.72 (d, 1H), 7.79 (s, 1H), 11.09 (s, 1H).
Workup
- customThe title compound was synthesized
- customCrude product was purified by chromatography (CombiFlash, 1st column silica, eluent: 0-10% MeOH/DCM; 2nd column C-18 RP eluent: 0-100% MeCN/water)
Sources & evidence
- ORD record
- ord-83c9be13b4e74c828ff51a32a8d97968
- Source dataset
- uspto-grants-2015_03
- Patent number
- US08975254B2
Reaction notes
Loading…