3-Amino-1,2-propanediol → 4-[[4-[(2,6-Dichlorophenyl)methyl]-6-(2,3-dihydroxypropylamino)-1,3,5-triazin-2-yl]amino]benzonitrile

HRID 25054

반응식

HRID 25054 반응식
Cl[C:2]1[N:7]=[C:6]([CH2:8][C:9]2[C:14]([Cl:15])=[CH:13][CH:12]=[CH:11][C:10]=2[Cl:16])[N:5]=[C:4]([NH:17][C:18]2[CH:25]=[CH:24][C:21]([C:22]#[N:23])=[CH:20][CH:19]=2)[N:3]=1.[NH2:26][CH2:27][CH:28]([OH:31])[CH2:29][OH:30]>O1CCOCC1.CN1CCCC1=O>[Cl:16][C:10]1[CH:11]=[CH:12][CH:13]=[C:14]([Cl:15])[C:9]=1[CH2:8][C:6]1[N:7]=[C:2]([NH:26][CH2:27][CH:28]([OH:31])[CH2:29][OH:30])[N:3]=[C:4]([NH:17][C:18]2[CH:25]=[CH:24][C:21]([C:22]#[N:23])=[CH:20][CH:19]=2)[N:5]=1

참가 물질

5

반응물 2

HCID 735613-Amino-1,2-propanediolHCID 4864234-[[4-Chloro-6-[(2,6-dichlorophenyl)methyl]-1,3,5-triazin-2-yl]amino]benzonitrile

생성물 1

HCID 5054184-[[4-[(2,6-Dichlorophenyl)methyl]-6-(2,3-dihydroxypropylamino)-1,3,5-triazin-2-yl]amino]benzonitrile수율 98.2%

시약·촉매·용매 2

HCID 13387N-methyl-2-pyrrolidone용매HCID 312751,4-Dioxane용매

실험 절차

A mixture of intermediate (27) (0.00256 mol) and 3-amino-1,2-propanediol (0.00563 mol) in 1,4-dioxane (10 ml) and 1-methyl-pyrrolidinone (2 ml) was stirred at RT for 48 hours under argon. The reaction mixture was concentrated, quenched with DCM/H2O and stirred. The precipitate was filtered off, yielding 1.12 g (86.9%) of (±)-4-[[4-[(2,6-dichlorophenyl)methyl]-6-[(2,3-dihydroxypropyl)amino]-1,3,5-triazin-2-yl]amino]benzonitrile (compound 26).

후처리

  1. concentrationThe reaction mixture was concentrated
  2. customquenched with DCM/H2O
  3. stirringstirred
  4. filtrationThe precipitate was filtered off

출처 및 근거

ORD 기록
ord-03bc4a0b0eb641639980ecae02ca4a58
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06858609B2

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