Dimethylacetamide → HCID 9890626, compound

HRID 967876Notes

Reaction equation

HRID 967876 reaction equation
FC(F)(F)C(O)=[O:4].O=S1(=O)CCNCC1.Cl[CH2:17][CH2:18][CH2:19][O:20][C:21]1[CH:49]=[CH:48][C:24]([C:25]([NH:27][C:28]2[CH:29]=[CH:30][C:31]([CH3:47])=[C:32]([NH:34][C:35](=[O:46])[C:36]3[CH:41]=[CH:40][C:39]([O:42][CH3:43])=[C:38]([O:44][CH3:45])[CH:37]=3)[CH:33]=2)=[O:26])=[CH:23][CH:22]=1.C(N(C(C)C)CC)(C)C.CC(N(C)C)=O>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[OH:4][CH2:17][CH2:18][CH2:19][O:20][C:21]1[CH:49]=[CH:48][C:24]([C:25]([NH:27][C:28]2[CH:29]=[CH:30][C:31]([CH3:47])=[C:32]([NH:34][C:35](=[O:46])[C:36]3[CH:41]=[CH:40][C:39]([O:42][CH3:43])=[C:38]([O:44][CH3:45])[CH:37]=3)[CH:33]=2)=[O:26])=[CH:23][CH:22]=1

Participants

7

Reactant 4

HCID 31374DimethylacetamideHCID 81531DiisopropylethylamineHCID 22291086HCID 22291086, compoundHCID 22498616Trifluoroacetic acid--1lambda~6~,4-thiazinane-1,1-dione (1/1)

Product 1

HCID 9890626HCID 9890626, compound

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

S,S-Dioxothiamorpholine trifluoroacetic acid salt (0.22 g) was added to a stirred mixture of N-{5-[4-(3-chloropropoxy)benzamido]-2-methylphenyl}-3,4-dimethoxybenzamide (0.5 g), tetra-n-butylammonium iodide (0.096 g), di-isopropylethylamine (0.29 g) and DMA (4 ml) and the mixture was stirred and heated to 100° C. for 1 week. The reaction mixture was allowed to cool to ambient temperature and poured into water (100 ml). The resultant precipitate was isolated and washed with water and with diethyl ether. The solid so obtained was purified by column chromatography on silica gel using increasingly polar mixtures of methylene chloride and methanol as eluent. There were thus obtained in turn:

Workup

  1. temperatureto cool to ambient temperature

Sources & evidence

ORD record
ord-4f590ae8def74c44a593d5d2e678000f
Source dataset
uspto-grants-2005_10
Patent number
US06956037B2

Reaction notes

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