tert-Butanol → tert-Butyl (3-Amino-1-phenyl-1H-pyrazol-4-yl)carbamate

HRID 1013488노트

반응식

HRID 1013488 반응식
[N+:1]([C:4]1[C:5](C(O)=O)=[N:6][N:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:8]=1)([O-])=O.C([N:20](CC)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.FC(F)(F)[C:44]([OH:46])=[O:45].[C:49](O)([CH3:52])([CH3:51])[CH3:50]>O1CCOCC1>[NH2:20][C:5]1[C:4]([NH:1][C:44](=[O:45])[O:46][C:49]([CH3:52])([CH3:51])[CH3:50])=[CH:8][N:7]([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:6]=1

참가 물질

7

반응물 5

HCID 6386tert-ButanolHCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 230849354-Nitro-1-phenyl-1H-pyrazole-3-carboxylic acid

생성물 1

HCID 57717456tert-Butyl (3-Amino-1-phenyl-1H-pyrazol-4-yl)carbamate

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

A solution of 4-nitro-1-phenyl-1H-pyrazole-3-carboxylic acid (20.0 g, 85.8 mmol), triethylamine (36.0 mL, 257.3 mmol), and diphenylphosphoryl azide (37.8 g, 137.2 mmol) in dioxane (400 mL) and tert-butanol (200 mL) was heated to reflux for 16 hours. The reaction was evaporated to dryness in vacuo, diluted with methylene chloride (400 mL) and treated with trifluoroacetic acid (128 g, 857.7 mmol). The solution was stirred at ambient temperature for 16 hours. The reaction was evaporated in vacuo and the resulting oil diluted with hexanes (750 mL), ethyl acetate (150 mL) and methylene chloride (100 mL). The solids were filtered, washed with above solvent system (hexanes:ethyl acetate; methylene chloride 75:15:10), and dried to give 12.0 g of desired product as yellow solid. 1H NMR (CDCl3) δ 8.43 (s, 1H), 7.62 (m, 2H), 7.48 (m, 2H), 7.37 (m, 1H).

후처리

  1. temperatureto reflux for 16 hours
  2. customThe reaction was evaporated to dryness in vacuo
  3. additiondiluted with methylene chloride (400 mL)
  4. customThe reaction was evaporated in vacuo
  5. additionthe resulting oil diluted with hexanes (750 mL), ethyl acetate (150 mL) and methylene chloride (100 mL)
  6. filtrationThe solids were filtered
  7. washwashed with above solvent system (hexanes:ethyl acetate; methylene chloride 75:15:10)
  8. customdried

출처 및 근거

ORD 기록
ord-588e3134367d4558b3947923e9a134c5
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07981874B2

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