3-Aminopyridine → Methyl 2-[(pyridin-3-ylamino)sulfonyl]benzoate

HRID 252207

반응식

HRID 252207 반응식
Cl[S:2]([C:5]1[CH:14]=[CH:13][CH:12]=[CH:11][C:6]=1[C:7]([O:9][CH3:10])=[O:8])(=[O:4])=[O:3].[N:15]1[CH:20]=[CH:19][CH:18]=[C:17]([NH2:21])[CH:16]=1>CC#N.CCOC(C)=O.CCOCC>[N:15]1[CH:20]=[CH:19][CH:18]=[C:17]([NH:21][S:2]([C:5]2[CH:14]=[CH:13][CH:12]=[CH:11][C:6]=2[C:7]([O:9][CH3:10])=[O:8])(=[O:4])=[O:3])[CH:16]=1

참가 물질

6

반응물 2

HCID 100093-AminopyridineHCID 117830Benzoic acid, 2-(chlorosulfonyl)-, methyl ester

생성물 1

HCID 4354882Methyl 2-[(pyridin-3-ylamino)sulfonyl]benzoate

시약·촉매·용매 3

HCID 3283Diethyl Ether용매HCID 6342Acetonitrile용매HCID 8857Ethyl Acetate용매

실험 절차

Methyl 2-(chlorosulfonyl)benzoate (14.1 g, 60.0 mmol) was added to a stirred solution of 3-pyridinamine (15.0 g, 159.4 mmol) in CH3CN (0.4 M). The temperature rose to 25° C. and a small amount of reddish oil separated out. CHCl3 (2.0 M, protected with amylenes) was added to return all materials to solution. After 1 h, the solvents were evaporated and the residual oil was partitioned between EtOAc and water. The organic layer was washed with water and was evaporated to give the crude product. The crude product was dissolved in the minimum amount of hot EtOAc and was diluted with ether. The product rapidly crystallized out and after 1 hour filtered off and washed with ether to provide the title compound. 1H NMR (400 MHz, CDCl3) δ 8.38 (d, 1H) 8.31 (d, 2H) 7.93 (d, 2H) 7.80 (d, 2H) 7.76 (t, 1H) 7.64 (t, 1H) 7.53 (t, 1H) 7.25 (m, 1H) 4.12 (s, 3H).

후처리

  1. customrose to 25° C.
  2. customa small amount of reddish oil separated out
  3. additionCHCl3 (2.0 M, protected with amylenes) was added
  4. customthe solvents were evaporated
  5. customthe residual oil was partitioned between EtOAc and water
  6. washThe organic layer was washed with water
  7. customwas evaporated
  8. customto give the crude product
  9. customThe product rapidly crystallized out and after 1 hour
  10. filtrationfiltered off
  11. washwashed with ether

출처 및 근거

ORD 기록
ord-98e7c2aab3264f9c8d39a0a5a61ac333
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07868026B2

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