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llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
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Triethylamine → N-[4-(2-Dimethylaminoethyl)-3,4-dihydro-3-methyl-2H-1,4-benzoxazin-6-yl]-2'-methyl-4'-(5-methyl-1,2,4-oxadiazol-3-yl)biphenyl-4-carboxamide

HRID 1292027
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HRID 1292027 반응식
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]2[N:12]=[C:11]([CH3:13])[O:10][N:9]=2)[CH:5]=[CH:4][C:3]=1[C:14]1[CH:19]=[CH:18][C:17]([C:20](O)=[O:21])=[CH:16][CH:15]=1.S(Cl)(Cl)=O.[NH2:27][C:28]1[CH:29]=[CH:30][C:31]2[O:36][CH2:35][CH:34]([CH3:37])[N:33]([CH2:38][CH2:39][N:40]([CH3:42])[CH3:41])[C:32]=2[CH:43]=1.C(N(CC)CC)C>ClCCl>[CH3:41][N:40]([CH3:42])[CH2:39][CH2:38][N:33]1[C:32]2[CH:43]=[C:28]([NH:27][C:20]([C:17]3[CH:16]=[CH:15][C:14]([C:3]4[CH:4]=[CH:5][C:6]([C:8]5[N:12]=[C:11]([CH3:13])[O:10][N:9]=5)=[CH:7][C:2]=4[CH3:1])=[CH:19][CH:18]=3)=[O:21])[CH:29]=[CH:30][C:31]=2[O:36][CH2:35][CH:34]1[CH3:37]
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참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 111301684-[2-methyl-4-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]benzoic AcidHCID 189140836-amino-3,4-dihydro-4-(2-dimethylaminoethyl)-3-methyl-2H-1,4-benzoxazine

생성물 1

HCID 18914091N-[4-(2-Dimethylaminoethyl)-3,4-dihydro-3-methyl-2H-1,4-benzoxazin-6-yl]-2'-methyl-4'-(5-methyl-1,2,4-oxadiazol-3-yl)biphenyl-4-carboxamide
수율 54.3%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

2'-Methyl-4'-(5-methyl-1,2,4-oxadiazol-3-yl)biphenyl-4-carboxylic acid (EP 0533268A1) (77 mg, 0.26 mmol) was treated with thionyl chloride (5 ml) and the mixture heated under reflux under Ar for 1 hour, then concentrated in vacuo to afford a yellow solid. This was dissolved in dichloromethane (5 ml) and treated with a solution of 6-amino-3,4-dihydro-4-(2-dimethylaminoethyl)-3-methyl-2H-1,4-benzoxazine (D14, 61.7 mg, 0.26 mmol) and triethylamine (0.11 ml, 0.78 inmol) in dichloromethane (10 ml). The reaction mixture was stirred at room temperature under Ar for 24 hours, then washed with brine/saturated potassium carbonate solution (30 ml of a 1:1 solution). The organic layer was separated, dried (Na2SO4) and concentrated in vacuo to afford a brown oil. This was chromatographed on SiO2, eluting with 0-8% methanol/dichloromethane to afford the title compound as a light yellow oil (72.2 mg, 54%).

후처리

  1. temperaturethe mixture heated
  2. temperatureunder reflux under Ar for 1 hour
  3. concentrationconcentrated in vacuo
  4. customto afford a yellow solid
  5. washwashed with brine/saturated potassium carbonate solution (30 ml of a 1:1 solution)
  6. customThe organic layer was separated
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated in vacuo
  9. customto afford a brown oil
  10. customThis was chromatographed on SiO2
  11. washeluting with 0-8% methanol/dichloromethane

출처 및 근거

ORD 기록
ord-a7f58dde311a4fb292bb758ff95ea4ec
출처 데이터셋
uspto-grants-1998_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05756496

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