Pyridine → HCID 57920370, 화합물

HRID 57179

반응식

HRID 57179 반응식
Cl.[CH3:2][C:3]1[C:4]2[CH:12]=[CH:11][CH:10]=[CH:9][C:5]=2[S:6][C:7]=1[NH2:8].N1C=CC=CC=1.Cl[S:20]([C:23]1[CH:31]=[CH:30][C:26]([C:27]([OH:29])=[O:28])=[CH:25][CH:24]=1)(=[O:22])=[O:21]>C1COCC1.CCOC(C)=O>[CH3:2][C:3]1[C:4]2[CH:12]=[CH:11][CH:10]=[CH:9][C:5]=2[S:6][C:7]=1[NH:8][S:20]([C:23]1[CH:24]=[CH:25][C:26]([C:27]([OH:29])=[O:28])=[CH:30][CH:31]=1)(=[O:22])=[O:21]

참가 물질

6

반응물 3

HCID 1049PyridineHCID 823854-(Chlorosulfonyl)benzoic acidHCID 567239383-Methyl-1-benzothiophen-2-amine hydrochloride

생성물 1

HCID 57920370HCID 57920370, 화합물수율 84.6%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8857Ethyl Acetate용매

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온도
5 °C

실험 절차

A 12-L 4-neck flask equipped with an overhead mechanical stirrer, N2 inlet/outlet adapter, and thermocouple was charged with THF (3.26 L) and compound 757-A (326 g, 1.6 mol) followed by pyridine (265 mL, 3.3 mol). The reaction mixture was cooled to 5° C. using a ice bath, to which was added a solution of 4-(chlorosulfonyl)benzoic acid (396 g, 1.8 mol) dissolved in THF (2.44 L), drop-wise. The reaction was allowed to stir at ambient temperature for 72 h, diluted with EtOAc (4 L), washed with 1N HCl (1 L), brine (1 L), the organic layer dried over Na2SO4, filtered and evaporated under reduced pressure. The crude residue was purified by triturating with EtOAc/heptane (1:1/1 L). The slurry was filtered, washed with heptane (2×250 mL) and dried in a vacuum oven at 40° C. for 18 h to afford 470 g of compound 306-C as a white solid. 1H-NMR (DMSO-d6): δ 13.51 (br s, 1H), 10.65 (br s, 1H), 8.12 (d, 2H), 7.86 (d, 2H), 7.83-7.79 (m, 1H), 7.66-7.63 (m, 1H), 7.37-7.33 (m, 1H), 2.03 (s, 3H).

후처리

  1. customA 12-L 4-neck flask equipped with an overhead mechanical stirrer, N2 inlet/outlet adapter
  2. washwashed with 1N HCl (1 L), brine (1 L)
  3. dry with materialthe organic layer dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customThe crude residue was purified
  7. customby triturating with EtOAc/heptane (1:1/1 L)
  8. filtrationThe slurry was filtered
  9. washwashed with heptane (2×250 mL)
  10. customdried in a vacuum oven at 40° C. for 18 h

출처 및 근거

ORD 기록
ord-64bc97dbf73749999ebe68314798e32e
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434711B2

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