Ethanethiol → 2-Hydroxymethyl-cyclopropanesulfonic acid [7-(2-fluoro-4-iodo-phenylamino)-6-methyl-5-oxo-2,3-dihydro-5H-oxazolo[3, 2-a]pyridin-8-yl]-amide

HRID 1259389노트

반응식

HRID 1259389 반응식
[F:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[C:11]([NH:21][S:22]([CH:25]2[CH2:27][CH:26]2[CH2:28][O:29]CC2C=CC=CC=2)(=[O:24])=[O:23])=[C:12]2[O:20][CH2:19][CH2:18][N:13]2[C:14](=[O:17])[C:15]=1[CH3:16].B(F)(F)F.C(S)C>C(OC(=O)C)C>[F:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[C:11]([NH:21][S:22]([CH:25]2[CH2:27][CH:26]2[CH2:28][OH:29])(=[O:24])=[O:23])=[C:12]2[O:20][CH2:19][CH2:18][N:13]2[C:14](=[O:17])[C:15]=1[CH3:16]

참가 물질

5

반응물 3

HCID 6343EthanethiolHCID 6356Boron trifluorideHCID 583805532-Benzyloxymethyl-cyclopropanesulfonic acid [7-(2-fluoro-4-iodo-phenylamino)-6-methyl-5-oxo-2,3-dihydro-5H-oxazolo[3,2-a]pyridin-8-yl]-amide

생성물 1

HCID 529340922-Hydroxymethyl-cyclopropanesulfonic acid [7-(2-fluoro-4-iodo-phenylamino)-6-methyl-5-oxo-2,3-dihydro-5H-oxazolo[3, 2-a]pyridin-8-yl]-amide수율 27%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

2-Benzyloxymethyl-cyclopropanesulfonic acid [7-(2-fluoro-4-iodo-phenylamino)-6-methyl-5-oxo-2,3-dihydro-5H-oxazolo[3,2-a]pyridin-8-yl]-amide (0.05 g, 0.0001 mol) was added to a stirred solution of BF3.EtO2 (0.34 g, 0.002 mol) in ethane thiol (0.05 g, 0.001 mol) at 0° C. under nitrogen atmosphere. The resulting mixture was stirred at room temperature overnight. The reaction was monitored by TLC (100% ethylacetate). The reaction mixture was quenched with saturated NaHCO3 solution and extracted with ethylacetate. The organic layer was washed with water, dried over Na2SO4 and concentrated. Purification by column chromatography on silica gel (2-3% MeOH in DCM) afforded 11 mg of the product (27% yield).

후처리

  1. customat 0° C.
  2. customThe reaction mixture was quenched with saturated NaHCO3 solution
  3. extractionextracted with ethylacetate
  4. washThe organic layer was washed with water
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customPurification by column chromatography on silica gel (2-3% MeOH in DCM)

출처 및 근거

ORD 기록
ord-d3373bbbd136424d8e303cf0efc5270f
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08466289B2

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