Acetic Anhydride → HCID 57397373, 화합물

HRID 2076035노트

반응식

HRID 2076035 반응식
[C:1](OC(=O)C)(=O)[CH3:2].[CH3:8][O:9][C:10]1[CH:19]=[C:18]([NH:20][C:21]2[S:22][C:23]3[CH2:29][CH2:28][CH2:27][CH:26]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[C:24]=3[N:25]=2)[CH:17]=[CH:16][C:11]=1[C:12]([NH:14][NH2:15])=[O:13]>CN(C)C=O>[CH3:8][O:9][C:10]1[CH:19]=[C:18]([NH:20][C:21]2[S:22][C:23]3[CH2:29][CH2:28][CH2:27][CH:26]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[C:24]=3[N:25]=2)[CH:17]=[CH:16][C:11]=1[C:12]1[O:13][C:1]([CH3:2])=[N:15][N:14]=1

참가 물질

4

반응물 2

HCID 7918Acetic AnhydrideHCID 86632604HCID 86632604, 화합물

생성물 1

HCID 57397373HCID 57397373, 화합물수율 65%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

At room temperature, acetic anhydride (108 μL) was added to a suspension of 2-methoxy-4-(4-phenyl-4,5,6,7-tetrahydro-benzothiazol-2-ylamino)-benzoic acid hydrazide (130 mg, 0.33 mmol) in dimethylformamide (5 mL). The mixture was stirred for 40 hours and evaporated to dryness. The residue was taken up in 10% w/w (3 mL) phosphorous pentoxide in methanesulfonic acid (prepared by mixing 5 g phosphorous pentoxide and 30 mL methanesulfonic acid and stirring for 2 h at 90° C.) and stirred for 18 hours. The mixture was poured into 75 ml water, neutralized to pH 5-6 with 32% aqueous sodium hydroxide and the precipitate filtered off. The solid was dissolved in ethyl acetate (30 mL), washed four times with water and once with brine, dried with magnesium sulfate and concentrated in vacuo, affording the title compound (69 mg, 65%) as an off-white solid. NMR (CDCl3, 300 MHz): δ (ppm)=7.74 (d, 1H), 7.61 (d, 1H), 7.31-7.15 (m, 5H), 6.82 (dd, 1H), 4.03 (m, 1H), 3.34 (m, 3H), 2.73 (m, 2H), 2.50 (m, 3H), 2.14 (m, 1H), 1.79 (m, 3H). MS ISP (m/e): 419.1 (100) (M+H)+.

후처리

  1. customevaporated to dryness
  2. customwas taken up in 10% w/w (3 mL) phosphorous pentoxide in methanesulfonic acid (prepared by mixing 5 g phosphorous pentoxide and 30 mL methanesulfonic acid and stirring for 2 h at 90° C.)
  3. stirringstirred for 18 hours
  4. additionThe mixture was poured into 75 ml water
  5. filtrationthe precipitate filtered off
  6. dissolutionThe solid was dissolved in ethyl acetate (30 mL)
  7. washwashed four times with water
  8. dry with materialonce with brine, dried with magnesium sulfate
  9. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-b3cba06d47aa436bb2cbc7508feb50ed
출처 데이터셋
uspto-grants-2011_04
특허 번호
US07923450B2

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