1-(4-Pyridinylmethyl)-1H-pyrazol-3-amine → HCID 86644390, compound

HRID 883052Notes

Reaction equation

COC[C@H](C)O[C:6]1[CH:7]=[C:8]([CH:12]=[C:13](O[C@@H](C)CC2C=CC=CC=2)[CH:14]=1)[C:9]([OH:11])=O.[N:26]1[CH:31]=[CH:30][C:29]([CH2:32][N:33]2[CH:37]=[CH:36][C:35]([NH2:38])=[N:34]2)=[CH:28][CH:27]=1>S(Cl)(Cl)=O>[N:26]1[CH:31]=[CH:30][C:29]([CH2:32][N:33]2[CH:37]=[CH:36][C:35]([NH:38][C:9](=[O:11])[C:8]3[CH:7]=[CH:6][CH:14]=[CH:13][CH:12]=3)=[N:34]2)=[CH:28][CH:27]=1

Participants

Conditions

Temperature: 70 °C

Procedure

3-((S)-2-Methoxy-1-methyl-ethoxy)-5-((S)-1-methyl-2-phenyl-ethoxy)-benzoic acid (0.58 mmol) is dissolved in thionylchloride (1.1 ml) and heated to 70° C. for 1 hour. After cooling to RT, the solvent is removed in vacuo. The residue is dissolved in dichloromethane (1.2 ml) and ethyldiisopropylamine (150 μl) is added and 1-pyridine-4-ylmethyl-1H-pyrazole-3-ylamine (1.2 eq.) is added. The suspension is stirred 4 days at room temperature. The reaction solution is extracted with water. The organic layer is washed with water and brine and dried over MgSO4 and the solvent is removed in vacuo. 3-(S)-2-Methoxy-1-methyl-ethoxy)-5-(S)-1-methyl-2-phenyl-ethoxy)-N-(1-pyridine-4-ylmethyl-1H-pyrazole-3-yl)-benzamide (“A8”) is isolated after column chromatography as colorless oil in a yield of 17%; HPLC (method B): 3.17 min; LC-MS (method B): 1.98 min, 501.3 (M+H+);

Workup

temperatureAfter cooling to RT
customthe solvent is removed in vacuo
dissolutionThe residue is dissolved in dichloromethane (1.2 ml)
additionethyldiisopropylamine (150 μl) is added
extractionThe reaction solution is extracted with water
washThe organic layer is washed with water and brine
dry with materialdried over MgSO4
customthe solvent is removed in vacuo

Sources & evidence

ORD record: ord-22361b3f420d4b65b25ae33f11165707
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08236824B2

Reaction notes

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