Triethylamine → 3-Benzyloxy-5-isopropoxy-N-(1-pyridine-2-ylmethyl-1H-pyrazole-3-yl)-benzamide

HRID 883045Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:15]=[C:16]([O:18][CH:19]([CH3:21])[CH3:20])[CH:17]=1)[C:12]([OH:14])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[N:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[CH2:35][N:36]1[CH:40]=[CH:39][C:38]([NH2:41])=[N:37]1.CCCCCCC.C(OCC)(=O)C>S(Cl)(Cl)=O>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:15]=[C:16]([O:18][CH:19]([CH3:21])[CH3:20])[CH:17]=1)[C:12]([NH:41][C:38]1[CH:39]=[CH:40][N:36]([CH2:35][C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][N:29]=2)[N:37]=1)=[O:14])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 70 °C

Procedure

1.4 3-Benzyloxy-5-isopropoxy-benzoic acid (0.86 mmol) is dissolved in thionyl chloride (1.6 ml) and heated to 70° C. for one hour. After cooling to RT, the solvent is removed in vacuo. The residue is dissolved in dichloromethane and triethylamine (1.5 eq.) and 1-pyridine-2-ylmethyl-1H-pyrazole-3-ylamine (1.2 eq.) are added. The reaction is stirred 16 hours at RT. 3-Benzyloxy-5-isopropoxy-N-(1-pyridine-2-ylmethyl-1H-pyrazole-3-yl)-benzamide is obtained after column chromatography (heptane/ethyl acetate) as a colorless powder in a yield of 43%; HPLC (Method B): 3.21 min; LC-MS: 2.285 min, 443.15 (M+H+);

Workup

temperatureAfter cooling to RT
customthe solvent is removed in vacuo
dissolutionThe residue is dissolved in dichloromethane

Sources & evidence

ORD record: ord-45aba3fb243e437ba7576118e0a71517
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08236824B2

Reaction notes

Loading…