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

HRID 571401ノート

反応式

HRID 571401 の反応式
[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

参加物

6

反応物 4

HCID 2346Benzyl IsothiocyanateHCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 895258183-(2-methylpyridin-4-yl)-1-trityl-1H-pyrazolo[4,3-c]pyridin-6-amine2 回

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
100 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-77265b85697b4309aa0698e1e7d5f137
出典データセット
uspto-grants-2015_05
特許番号
US09023865B2

反応ノート

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