Dimethylformamide → HCID 59577934, compound

HRID 2194131Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([N:11]1[CH2:21][CH2:20][C:14]2([C:18](=[O:19])[NH:17][CH2:16][CH2:15]2)[CH2:13][CH2:12]1)(=[O:10])=[O:9].C1([C:25]2[CH:30]=[CH:29][C:28](I)=[CH:27][C:26]=2[CH2:32][O:33][CH3:34])CC1.CN[CH2:37][CH2:38]NC.[O-]P([O-])([O-])=O.[K+].[K+].[K+].[CH3:49]N(C=O)C>CCOC(C)=O.[Cu]I>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([N:11]1[CH2:21][CH2:20][C:14]2([C:18](=[O:19])[N:17]([C:29]3[CH:30]=[CH:25][C:26]([CH2:32][O:33][CH2:34][CH:38]4[CH2:37][CH2:49]4)=[CH:27][CH:28]=3)[CH2:16][CH2:15]2)[CH2:13][CH2:12]1)(=[O:9])=[O:10]

Participants

Conditions

Temperature: 145 °C

Procedure

A mixture of 8-(2-chloro-benzenesulfonyl)-2,8-diaza-spiro[4.5]decan-1-one (0.2 g), 1-cyclopropyl-methoxymethyl-4-iodo-benzene (0.351 g), N,N′-dimethylethylenediamine (0.107 g), K3PO4 (0.387 g) and CuI (0.174 g) in DMF (10 ml) under an argon atmosphere was stirred at 145° C. for five hours until conversion was complete. The reaction mixture was cooled to RT, taken up in AcOEt (120 ml) which was then washed twice with water (each 50 ml). The organic layer was dried over magnesium sulphate and the solvent was removed in vacuo. The residue was chromatographed on silica gel (AcOEt/Heptane, gradient from 0 to 25%,) to give the desired 8-(2-chloro-benzenesulfonyl)-2-(4-cyclopropylmethoxymethyl-phenyl)-2,8-diaza-spiro[4.5]decan-1-one (0.128 g) as a white solid. MS (ESI): 489.3 MH+).

Workup

temperatureThe reaction mixture was cooled to RT
washwas then washed twice with water (each 50 ml)
dry with materialThe organic layer was dried over magnesium sulphate
customthe solvent was removed in vacuo
customThe residue was chromatographed on silica gel (AcOEt/Heptane, gradient from 0 to 25%,)

Sources & evidence

ORD record: ord-dd2b189a93ae4d8d85d03a7c5ef95a35
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08329904B2

Reaction notes

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