Diisopropylethylamine → HCID 71279164, compound

HRID 1621117Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([CH3:14])[C:10]=1[C:11]([OH:13])=O)=[O:5])[CH3:2].Cl.[CH3:16][C:17]1[O:21][C:20]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[N:19][C:18]=1[CH2:28][CH2:29][NH2:30].CCCP1(OP(CCC)(=O)OP(CCC)(=O)O1)=O.C(N(CC)C(C)C)(C)C.OS([O-])(=O)=O.[K+]>C1COCC1>[CH3:14][N:9]1[C:10]([C:11](=[O:13])[NH:30][CH2:29][CH2:28][C:18]2[N:19]=[C:20]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[O:21][C:17]=2[CH3:16])=[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH:7]=[N:8]1

Participants

Conditions

Temperature: 70 °C

Procedure

To a suspension of 4-(ethoxycarbonyl)-1-methyl-1H-pyrazole-5-carboxylic acid (500 mg, 2.52 mmol, prepared as described in US 2011/0071128) in THF (12.5 mL) were added 2-(5-methyl-2-phenyloxazol-4-yl)ethanamine hydrochloride (602 mg, 2.52 mmol), 1-propanephosphonic acid cyclic anhydride (4.01 g, 3.75 mL, 6.31 mmol) and N,N-diisopropylethylamine (2.61 g, 3.53 mL, 20.2 mmol) at RT. The mixture was stirred at 70° C. for 2 h, poured into KHSO4 (10% aqueous solution, 50 mL) and extracted with ethyl acetate (2×75 mL). The organic phases were washed with water (50 mL) and brine (50 mL). The combined organic layer was dried over MgSO4 and concentrated in vacuo to give 735 mg crude product. The product was obtained after purification by flash chromatography (using silica gel and an ethyl acetate/heptane gradient) as white solid (410 mg, 1.07 mmol, 42.5%).

Workup

extractionextracted with ethyl acetate (2×75 mL)
washThe organic phases were washed with water (50 mL) and brine (50 mL)
dry with materialThe combined organic layer was dried over MgSO4
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-6888cd556f324aaf8c739e0a1440fe53
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08772510B2

Reaction notes

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