Hydrochloric Acid → 4-((1R,2R)-2-Methyl-cyclohexylamino)-3-(2-thiazol-5-yl-acetylamino)-benzoic acid methyl ester

HRID 1750231노트

반응식

HRID 1750231 반응식
[S:1]1[C:5]([CH2:6][C:7]([OH:9])=O)=[CH:4][N:3]=[CH:2]1.C1C=NC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[CH3:29][O:30][C:31](=[O:47])[C:32]1[CH:37]=[CH:36][C:35]([NH:38][C@@H:39]2[CH2:44][CH2:43][CH2:42][CH2:41][C@H:40]2[CH3:45])=[C:34]([NH2:46])[CH:33]=1.Cl>CN(C=O)C.O.C(Cl)CCl>[CH3:29][O:30][C:31](=[O:47])[C:32]1[CH:37]=[CH:36][C:35]([NH:38][C@@H:39]2[CH2:44][CH2:43][CH2:42][CH2:41][C@H:40]2[CH3:45])=[C:34]([NH:46][C:7](=[O:9])[CH2:6][C:5]2[S:1][CH:2]=[N:3][CH:4]=2)[CH:33]=1

참가 물질

9

반응물 5

HCID 313Hydrochloric AcidHCID 81531Diisopropylethylamine2회HCID 181649HOAtHCID 3494395-Thiazoleacetic acidHCID 867144383-Amino-4-((1R,2R)-2-methyl-cyclohexylamino)-benzoic acid methyl ester

생성물 1

HCID 867144394-((1R,2R)-2-Methyl-cyclohexylamino)-3-(2-thiazol-5-yl-acetylamino)-benzoic acid methyl ester수율 94.2%

시약·촉매·용매 3

HCID 111,2-Dichloroethane용매HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

To a solution of 0.49 g of thiazol-5-yl-acetic acid in 10 ml of dry DMF 0.27 g of HOAT, 0.79 g of EDC and 1 ml of DIPEA were added at 0° C. After 30 min 0.9 g of 3-Amino-4-((1R,2R)-2-methyl-cyclohexylamino)-benzoic acid methyl ester were added, followed by the addition of 1 ml of DIPEA and the reaction was stirred at it for 48 h. The reaction was then poured into water, brought to pH3 by the addition of 2 M aqueous hydrochloric acid and extracted with ethyl acetate three times. The combined organic phases were washed with saturated aqueous sodium bicarbonate solution and brine, dried over magnesium sulphate and concentrated to obtain 1.25 g (94%) of 4-((1R,2R)-2-Methyl-cyclohexylamino)-3-(2-thiazol-5-yl-acetylamino)-benzoic acid methyl ester, which was used without further purification.

후처리

  1. extractionextracted with ethyl acetate three times
  2. washThe combined organic phases were washed with saturated aqueous sodium bicarbonate solution and brine
  3. dry with materialdried over magnesium sulphate
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-af0b6516e9d34932a841b7534eb9a1bc
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09156796B2

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