Triethylamine → {6-Oxo-1-propyl-8-[1-(3-trifluoromethyl-benzyl)-1H-pyrazol-4-yl]-6,7-dihydro-1H-purin-2-ylamino}-acetic acid ethyl ester

HRID 536023Notes

Reaction equation

Cl[C:2]1[N:3]([CH2:28][CH2:29][CH3:30])[C:4](=[O:27])[C:5]2[NH:6][C:7]([C:11]3[CH:12]=[N:13][N:14]([CH2:16][C:17]4[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[CH:18]=4)[CH:15]=3)=[N:8][C:9]=2[N:10]=1.[CH2:31](N(CC)CC)[CH3:32].Cl.C([NH:41][CH2:42][C:43]([OH:45])=[O:44])C.C(OCC)(=O)C>CN1C(=O)CCC1>[CH2:31]([O:45][C:43](=[O:44])[CH2:42][NH:41][C:2]1[N:3]([CH2:28][CH2:29][CH3:30])[C:4](=[O:27])[C:5]2[NH:6][C:7]([C:11]3[CH:12]=[N:13][N:14]([CH2:16][C:17]4[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:24])[F:25])[CH:18]=4)[CH:15]=3)=[N:8][C:9]=2[N:10]=1)[CH3:32]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 2-Chloro-1-propyl-8-[1-(3-trifluoromethyl-benzyl)-1H-pyrazol-4-yl]-1,7-dihydro-purin-6-one (0.1 g, 0.22 mmol) in NMP (1.5 ml) under argon was added triethyl amine (0.113 g, 1.118 mmol) and ethyl glycine hydrochloride (0.096 g, 0.68 mmol). The reaction mixture was heated at 100° C. for 16 hours. To the reaction mixture ethyl acetate was added and it was washed with water and brine. Ethyl acetate layer was dried over sodium sulphate, filtered and concentrated under reduced pressure and residue obtained was purified by column chromatography to obtain {6-Oxo-1-propyl-8-[1-(3-trifluoromethyl-benzyl)-1H-pyrazol-4-yl]-6,7-dihydro-1H-purin-2-ylamino}-acetic acid ethyl ester (0.080 g, 69%) as an off white solid.

Workup

washit was washed with water and brine
dry with materialEthyl acetate layer was dried over sodium sulphate
filtrationfiltered
concentrationconcentrated under reduced pressure and residue
customobtained
customwas purified by column chromatography

Sources & evidence

ORD record: ord-a81419025c1c43668301f3a729c0da43
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08859566B2

Reaction notes

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