Triethylamine → HCID 22484115, 화합물

HRID 2181359노트

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HRID 2181359 반응식
[CH3:1][N:2]1[C:7](=[O:8])[C:6]2[C:9](C(O)=O)=[C:10]([CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[C:19]([F:22])([F:21])[F:20])[S:11][C:5]=2[N:4]([CH2:26][CH:27]([CH3:29])[CH3:28])[C:3]1=[O:30].C([N:33](CC)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.ClCCl.CCCC(C)C>C(O)(C)(C)C>[NH2:33][C:9]1[C:6]2[C:7](=[O:8])[N:2]([CH3:1])[C:3](=[O:30])[N:4]([CH2:26][CH:27]([CH3:28])[CH3:29])[C:5]=2[S:11][C:10]=1[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[C:19]([F:20])([F:21])[F:22]

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 52825261,2,3,4-Tetrahydro-3-methyl-1-(2-methylpropyl)-2,4-dioxo-6-[[2-(trifluoromethyl)phenyl]methyl]thieno[2,3-d]pyrimidine-5-carboxylic acidHCID 86592985Dichloromethane isohexane

생성물 1

HCID 22484115HCID 22484115, 화합물

시약·촉매·용매 1

HCID 6386tert-Butanol용매

실험 절차

1,2,3,4-Tetrahydro-3-methyl-1-(2-methylpropyl)-2,4-dioxo-6-[[2-(trifluoromethyl)phenyl]methyl]-thieno[2,3-d]pyrimidine-5-carboxylic acid made by the method of Example 8a) (3.316 g), triethylamine (1.38 ml) and diphenylphosphoryl azide (2.26 ml) were heated at 90° C. under an atmosphere of nitrogen in tert-butanol for 18 hrs. The reaction was concentrated in vacuo and the residue redissolved in dichloromethane (50 ml) and trifluoroacetic acid (30 ml). The mixture was allowed to stir for 36 hrs before being concentrated in vacuo, and residual acid was removed by azeotroping with toluene. The residue was partitioned between half saturated sodium hydrogen carbonate and dichloromethane. The organics were collected, dried over magnesium sulfate and concentrated in vacuo. The crude product was purified by chromatography, eluting with 2:1 isohexane:diethyl ether to yield a highly crystalline solid which was recystallised from dichloromethane/isohexane to yield the subtitle compound (1.553 g).

후처리

  1. concentrationThe reaction was concentrated in vacuo
  2. dissolutionthe residue redissolved in dichloromethane (50 ml)
  3. concentrationbefore being concentrated in vacuo, and residual acid
  4. customwas removed
  5. customby azeotroping with toluene
  6. customThe residue was partitioned between half saturated sodium hydrogen carbonate and dichloromethane
  7. customThe organics were collected
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated in vacuo
  10. customThe crude product was purified by chromatography
  11. washeluting with 2:1 isohexane
  12. customdiethyl ether to yield a highly crystalline solid which

출처 및 근거

ORD 기록
ord-4ca38bbf5eff4cfda6af325c1aed0113
출처 데이터셋
uspto-grants-2005_05
특허 번호
US06890923B2

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