Methanol → HCID 69187894, 화합물

HRID 1020274노트

반응식

HRID 1020274 반응식
[F:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][CH:20]=1)[CH2:5][NH:6][C:7]([NH:9][C:10]1[S:14][N:13]=[C:12]([CH2:15][NH:16][CH3:17])[N:11]=1)=[O:8].CO.[CH3:23][C:24]1[C:28]([CH:29]=O)=[C:27]([CH3:31])[O:26][N:25]=1.C([BH3-])#N.[Na+]>C(Cl)Cl.C(O)(=O)C>[CH3:23][C:24]1[C:28]([CH2:29][N:16]([CH2:15][C:12]2[N:11]=[C:10]([NH:9][C:7]([NH:6][CH2:5][C:4]3[CH:18]=[CH:19][CH:20]=[C:2]([F:1])[CH:3]=3)=[O:8])[S:14][N:13]=2)[CH3:17])=[C:27]([CH3:31])[O:26][N:25]=1

참가 물질

7

반응물 4

HCID 887MethanolHCID 2895763,5-Dimethyl-4-Isoxazolecarbaldehyde2회HCID 5003444Sodium cyanoborohydride2회HCID 58055092HCID 58055092, 화합물2회

생성물 1

HCID 69187894HCID 69187894, 화합물

시약·촉매·용매 2

HCID 176Acetic Acid촉매HCID 6344Dichloromethane용매

실험 절차

1-(3-Fluoro-benzyl)-3-(3-methylaminomethyl-[1,2,4]thiadiazol-5-yl)-urea (Intermediate XXVII) was taken up in DCM and methanol with 3,5-Dimethyl-isoxazole-4-carbaldehyde (2 eq.) and acetic acid (several drops). Reaction was stirred for several hours at ambient temperature. Sodium cyanoborohydride (2 eq.) was added at once and the reaction was stirred overnight at ambient temperature. An additional equivalent of 3,5-Dimethyl-isoxazole-4-carbaldehyde and sodium cyanoborohydride (2 eq.) was added and stirred 4 more hours. Crude r×n mixture was loaded directly onto a silica plug and eluted with 10% saturated NH3/MeOH in DCM. Purified by column chromatography (silica, DCM, 0-10% MeOH saturated with NH3) to give the title compound. 1H NMR (400 MHz, DMSO): 11.45 (br s, 1H), 7.43-7.35 (m, 2H), 7.17-7.05 (m, 3H), 4.38 (d, 2H), 3.58 (s, 2H), 3.33 (s, 2H), 2.31 (s, 3H), 2.16 (s, 3H), 2.15 (s, 3H).

후처리

  1. customReaction
  2. stirringwas stirred overnight at ambient temperature
  3. stirringstirred 4 more hours
  4. washeluted with 10% saturated NH3/MeOH in DCM
  5. customPurified by column chromatography (silica, DCM, 0-10% MeOH saturated with NH3)

출처 및 근거

ORD 기록
ord-81710926290a45569c2e8327ca1ed29d
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08716320B2

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