1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 86656249, 화합물

HRID 79073노트

반응식

HRID 79073 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:15]2[CH:16]=[N:17][S:18][C:14]=2[CH:13]=[CH:12][C:11]=1[C:19]([OH:21])=O.C(N(C(C)C)CC)(C)C.C1C=CC2[N:39]([OH:40])N=NC=2C=1.[CH3:41][C:42]1([CH3:50])[O:46][C@H:45]([CH2:47]NO)[CH2:44][O:43]1.CCN=C=NCCCN(C)C>CN(C=O)C.C(OCC)(=O)C>[CH3:50][C:42]1([CH3:41])[O:46][C@@H:45]([CH2:47][O:40][NH:39][C:19]([C:11]2[CH:12]=[CH:13][C:14]3[S:18][N:17]=[CH:16][C:15]=3[C:10]=2[NH:9][C:3]2[CH:4]=[CH:5][C:6]([I:8])=[CH:7][C:2]=2[F:1])=[O:21])[CH2:44][O:43]1

참가 물질

8

반응물 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 23541087(S)-(+)-2,2-Dimethyl-4-hydroxyaminomethyl-1,3-dioxolaneHCID 670836404-(2-Fluoro-4-iodo-phenylamino)-benzo[d]isothiazole-5-carboxylic acid

생성물 1

HCID 86656249HCID 86656249, 화합물수율 43.3%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 4-(2-fluoro-4-iodo-phenylamino)-benzo[d]iso-thiazole-5-carboxylic acid (250 mg, 0.604 mmol), diisopropylethylamine (0.42 mL, 2.42 mmol), HOBt (163 mg, 0.1.21 mmol) and O—(((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-hydroxylamine (178 mg, 1.21 mmol) in DMF (2 mL) was added EDCI (232 mg, 1.21 mmol). The reaction mixture was stirred for 16 hours at room temperature, diluted with ethyl acetate, and washed with water, a saturated aqueous solution of sodium hydrogen carbonate, then brine before being dried (Na2SO4), filtered and concentrated in vacuo. The resultant residue was subjected to flash chromatography (Si—PPC, gradient 0% to 50%, EtOAc in cyclohexane) to afford the title compound as a solid (142 mg, 43%). LCMS (method B): RT=3.92 min, [M+H]+=544.

후처리

  1. washwashed with water
  2. dry with materiala saturated aqueous solution of sodium hydrogen carbonate, then brine before being dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-7fcc68027f4c4030b17169ff07a82d27
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841462B2

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