1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 86656247, 화합물

HRID 79063노트

반응식

HRID 79063 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.CCN(C(C)C)C(C)C.[CH:31]([O:33][CH2:34][CH2:35][O:36][NH2:37])=[CH2:32].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C>C1COCC1>[CH:31]([O:33][CH2:34][CH2:35][O:36][NH:37][C:19]([C:11]1[CH:12]=[CH:13][C:14]2[S:18][N:17]=[CH:16][C:15]=2[C:10]=1[NH:9][C:3]1[CH:4]=[CH:5][C:6]([I:8])=[CH:7][C:2]=1[F:1])=[O:21])=[CH2:32]

참가 물질

7

반응물 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 21867017O-(2-(Vinyloxy)ethyl)hydroxylamineHCID 670836404-(2-Fluoro-4-iodo-phenylamino)-benzo[d]isothiazole-5-carboxylic acid

생성물 1

HCID 86656247HCID 86656247, 화합물수율 89.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 4-(2-fluoro-4-iodo-phenylamino)-benzo[d]isothiazole-5-carboxylic acid (240 mg, 0.58 mmol) in THF (6 mL) was added DIPEA (396 μL, 2.34 mmol), O-(2-vinyloxy-ethyl)-hydroxylamine (119 mg, 1.15 mmol), HOBt (156 mg, 1.15 mmol) and EDCI (221 mg, 1.15 mmol) before the reaction mixture was stirred at room temperature for 18 hours. The reaction mixture was concentrated in vacuo and the resultant residue was partitioned between ethyl acetate and water. The organic extract was washed with aqueous saturated sodium bicarbonate solution then water, dried (Na2SO4) and concentrated in vacuo. The resultant residue was subjected to flash chromatography (Si—SPE, gradient 0-10% methanol in DCM) to yield the title compound (258 mg, 89%). LCMS (Method B): RT=3.83 min, [M+H]+=500.

후처리

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe resultant residue was partitioned between ethyl acetate and water
  3. extractionThe organic extract
  4. washwas washed with aqueous saturated sodium bicarbonate solution
  5. dry with materialwater, dried (Na2SO4)
  6. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-f26f1f662b3b4d7a8b7405446bd62854
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841462B2

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