Benzyl Isothiocyanate → 6-[(benzylcarbamothioyl)amino]-3-(2-methylpyridin-4-yl)-1H-pyrazolo[4,3-c]pyridin-5-ium trifluoroacetate

HRID 571401노트

반응식

HRID 571401 반응식
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]2[C:12]3[CH:13]=[N:14][C:15]([NH2:17])=[CH:16][C:11]=3[N:10](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[N:9]=2)[CH:5]=[CH:4][N:3]=1.[N:37]([CH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)=[C:38]=[S:39].[C:47]([OH:53])([C:49]([F:52])([F:51])[F:50])=[O:48].C([SiH](CC)CC)C>C1(C)C=CC=CC=1>[F:50][C:49]([F:52])([F:51])[C:47]([O-:53])=[O:48].[CH2:40]([NH:37][C:38]([NH:17][C:15]1[NH+:14]=[CH:13][C:12]2[C:8]([C:6]3[CH:5]=[CH:4][N:3]=[C:2]([CH3:1])[CH:7]=3)=[N:9][NH:10][C:11]=2[CH:16]=1)=[S:39])[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1

참가 물질

6

반응물 4

HCID 2346Benzyl IsothiocyanateHCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 895258183-(2-methylpyridin-4-yl)-1-trityl-1H-pyrazolo[4,3-c]pyridin-6-amine2회

생성물 1

HCID 1176016386-[(benzylcarbamothioyl)amino]-3-(2-methylpyridin-4-yl)-1H-pyrazolo[4,3-c]pyridin-5-ium trifluoroacetate수율 27%

시약·촉매·용매 1

HCID 1140Toluene용매

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온도
100 °C

실험 절차

A suspension of 3-(2-methylpyridin-4-yl)-1-trityl-1H-pyrazolo[4,3-c]pyridin-6-amine (intermediate 5a; 25 mg, 0.05 mmol) in toluene (1 mL) was treated with (isothiocyanatomethyl)benzene (15 mg, 0.1 mmol) and the mixture was heated at 100° C. overnight. The volatiles were concentrated in vacuo and the residue was directly dissolved in DCM (0.8 mL), treated with TFA (0.2 mL) and triethylsilane (0.008 mL, 0.051 mmol) and left under stirring for 5 h, then concentrated in vacuo and purified by MS-directed reverse phase preparative-HPLC (C-18 stationary phase, eluting with a H2O/MeCN gradient with 0.1% TFA) to yield 6-[(benzylcarbamothioyl)amino]-3-(2-methylpyridin-4-yl)-1H-pyrazolo[4,3-c]pyridin-5-ium trifluoroacetate as a yellow solid (7 mg, 0.014 mmol, 27%). MS ESI calc'd. for C20H19N6S [M+1]+ 375, found 375.

후처리

  1. concentrationThe volatiles were concentrated in vacuo
  2. dissolutionthe residue was directly dissolved in DCM (0.8 mL)
  3. waitleft
  4. concentrationconcentrated in vacuo
  5. custompurified by MS-directed reverse phase preparative-HPLC (C-18 stationary phase
  6. washeluting with a H2O/MeCN gradient with 0.1% TFA)

출처 및 근거

ORD 기록
ord-77265b85697b4309aa0698e1e7d5f137
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09023865B2

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