Water → HCID 59577874, compound

HRID 2194142Notes

Reaction equation

CO[C:3](=[O:31])[C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:14][CH2:13][C:12]3([CH2:19][CH2:18][N:17]([S:20]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=4[Cl:29])(=[O:22])=[O:21])[CH2:16][CH2:15]3)[C:11]2=[O:30])=[CH:6][CH:5]=1.[CH:32]([NH2:35])([CH3:34])[CH3:33].[Cl-].C[Al+]C.O>C1(C)C=CC=CC=1.CCCCCC>[Cl:29][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=1[S:20]([N:17]1[CH2:18][CH2:19][C:12]2([C:11](=[O:30])[N:10]([C:7]3[CH:6]=[CH:5][C:4]([C:3]([NH:35][CH:32]([CH3:34])[CH3:33])=[O:31])=[CH:9][CH:8]=3)[CH2:14][CH2:13]2)[CH2:15][CH2:16]1)(=[O:22])=[O:21]

Participants

Conditions

Temperature: 95 °C

Procedure

4-[8-(2-Chloro-benzenesulfonyl)-1-oxo-2,8-diaza-spiro[4.5]dec-2-yl]-benzoic acid methyl ester (0.149 g), compound of example 150), was suspended in toluene under an argon atmosphere at RT, isopropylamine (0.057 g) and dimethylaluminium chloride in hexane (1 molar, 1.61 ml) were added and the mixture stirred 10 minutes at 130° than overnight at 95° C. The reaction mixture was cooled to RT, water (0.05 ml) was added, and the mixture was stirred for 10 minutes. Then the solvent was carefully evaporated off in vacuo, the residue was adsorbed on silica gel and chromatographed over silica gel (eluents: AcOEt/heptane, gradient from 0 to 50%) to give the desired compound (0.048 g) as white solid. MS (ESI): 490.15 MH+).

Workup

temperatureThe reaction mixture was cooled to RT
stirringthe mixture was stirred for 10 minutes
customThen the solvent was carefully evaporated off in vacuo
customchromatographed over silica gel (eluents: AcOEt/heptane, gradient from 0 to 50%)

Sources & evidence

ORD record: ord-9ffdfea84f494c99b71c323e36e6e932
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08329904B2

Reaction notes

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