Hydrochloric Acid → HCID 44555483, 화합물

HRID 1966880노트

반응식

HRID 1966880 반응식
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[S:13][CH:14]=[N:15][N:16]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[C:17](Cl)(=[O:27])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26].Cl>N1C=CC=CC=1>[S:13]1[CH:14]=[N:15][N:16]=[C:12]1[NH:11][S:8]([C:5]1[CH:6]=[CH:7][C:2]([NH:1][C:17](=[O:27])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[CH:3][CH:4]=1)(=[O:10])=[O:9]

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 66982Decanoyl chlorideHCID 2347622-Sulfanilamido-1,3,4-thiadiazole

생성물 1

HCID 44555483HCID 44555483, 화합물수율 100%

시약·촉매·용매 1

HCID 1049Pyridine용매

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온도
95 °C

실험 절차

Compound 100 (50 mg, 0.20 mmol) was suspended in pyridine (0.3 mL). Decanoyl chloride (39.1 mg, 0.21 mmol) was added gradually over 15 min. The reaction mixture was heated to 95° C. and stirred at this temperature for 1 h, then poured into 10% aqueous HCl solution and extracted with EtOAc (3×0.5 mL). The combined organic extracts were washed with water (3×5 mL), brine (3×5 mL), and dried over anhydrous Na2SO4. Evaporation of the solvent yielded the product (80 mg, 0.20 mmol, 95%). It was recrystallized from hexanes/ethyl acetate to yield an analytical sample, mp 151-152° C.; 1H NMR (250 MHz, CD3OD) δ 0.88 (3, t, J=7.5 Hz), 1.24-1.45 (12, m), 1.68 (2, t, J=7.5 Hz), 2.37 (2, t, J=7.5 Hz), 7.72 (2, d, J=8.5 Hz), 7.79 (2, d, J=8.5 Hz), 8.49 (1, S); 13C NMR (125 MHz, CD3OD) δ 14.4, 23.7, 26.7, 30.3, 30.4, 30.5, 30.6, 33.0, 38.1, 102.4, 128.3, 137.5, 144.0, 145.0, 170.0, 174.9; MS (ESI+) 411.1 (M+H)+; HRMS (IonSpec. HiRES ESL+) calcd. for C18H27N4O3S2 (M+H)+411.1525, obsd. 411.1524.

후처리

  1. extractionextracted with EtOAc (3×0.5 mL)
  2. washThe combined organic extracts were washed with water (3×5 mL), brine (3×5 mL)
  3. dry with materialdried over anhydrous Na2SO4
  4. customEvaporation of the solvent

출처 및 근거

ORD 기록
ord-645bc2d83c2b46139de295e45f680c1c
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08420678B2

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