1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 86656249、化合物

HRID 79073ノート

反応式

HRID 79073 の反応式
[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

参加物

8

反応物 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

生成物 1

HCID 86656249HCID 86656249、化合物収率 43.3%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-7fcc68027f4c4030b17169ff07a82d27
出典データセット
uspto-grants-2014_09
特許番号
US08841462B2

反応ノート

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