Azido(trimethyl)stannane → HCID 178418841, 화합물

HRID 11125

반응식

HRID 11125 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:20]2[C:21](=[O:25])[NH:22][C:23](=[O:24])[C:19]=2[C:18]2[C:17]3[CH:16]=[C:15]([OH:26])[CH:14]=[CH:13][C:12]=3[N:11]([CH2:27][CH2:28][C:29]#[N:30])[C:10]=2[CH:9]=1.[N:31]([Sn](C)(C)C)=[N+:32]=[N-:33]>C1(C)C=CC=CC=1.CN(C)C=O.O.C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:20]2[C:21](=[O:25])[NH:22][C:23](=[O:24])[C:19]=2[C:18]2[C:17]3[CH:16]=[C:15]([OH:26])[CH:14]=[CH:13][C:12]=3[N:11]([CH2:27][CH2:28][C:29]3[NH:33][N:32]=[N:31][N:30]=3)[C:10]=2[CH:9]=1

참가 물질

6

반응물 2

HCID 5104973Azido(trimethyl)stannane2회HCID 248846973-(4-(2-Chlorophenyl)-9-hydroxy-1,3-dioxo-2,3-dihydropyrrolo[3,4-c]carbazol-6(1H)-yl)propanenitrile

생성물 1

HCID 178418841HCID 178418841, 화합물수율 72.2%

시약·촉매·용매 3

HCID 962Water용매HCID 8857Ethyl Acetate용매HCID 21735183Dimethylformamide toluene용매

실험 절차

To a solution of nitrile (238) (0.68 g, 1.63 mmol) prepared as described in example 98 in toluene/dimethylformamide (5:1, 120 mL) was added azidotrimethyl tin (0.67 g, 3.26 mmol). The resulting solution was heated at reflux for 24 hours before a further portion of azidotrimethyl tin (0.34 g, 1.63 mmol) was added. After a further 24 hours at reflux the reaction was diluted with water and extraction with ethyl acetate. The organic phase was dried, the drying agent was removed and the solution was concentrated to dryness. Chromatography on silica eluting with ethyl acetatelhexane (3:1) to ethyl acetate/methanol (9:1), followed by crystallization from ethyl acetate/hexane, gave tetrazole (272) (0.54 g, 72%) as an orange powder, mp 230–234° C. (dec). 1H NMR δ [(CD3)2SO] 11.06 (br s, 1H), 9.37 (br s, 1H), 8.36 (d, J=2.4 Hz, 1H), 7.61 (s, 1H), 7.56 (m, 1H), 7.48 (m, 4H), 7.10 (dd, J=8.8, 2.4 Hz, 1H), 4.82 (t, J=6.9 Hz, 2H), 3.32 (obscured t, J=6.9 Hz, 2H). Found: C, 52.69; H, 4.05; N, 15.91. C23H15ClN6O3.31/2H2O requires: C, 52.93; H, 4.25; N, 16.09.

후처리

  1. temperatureThe resulting solution was heated
  2. additionwas added
  3. temperatureAfter a further 24 hours at reflux the reaction
  4. customThe organic phase was dried
  5. customthe drying agent was removed
  6. concentrationthe solution was concentrated to dryness
  7. customChromatography on silica eluting with ethyl acetatelhexane (3:1) to ethyl acetate/methanol (9:1), followed by crystallization from ethyl acetate/hexane

출처 및 근거

ORD 기록
ord-48da5ed2f8704646a3a54504d181f110
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07094798B1

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