Diisopropylethylamine → HCID 66711936、化合物

HRID 1262113

反応式

HRID 1262113 の反応式
[C:1]([NH:5][S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]2[N:23]3[C:18]([CH:19]=[N:20][C:21](O)=[N:22]3)=[CH:17][CH:16]=2)[CH:10]=1)(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)C(C)C)(C)C.[N-](S(C(F)(F)F)(=O)=O)S(C(F)(F)F)(=O)=O.[CH3:49][O:50][C:51]1[CH:56]=[C:55]([CH:57]2[CH2:62][CH2:61][N:60]([CH3:63])[CH2:59][CH2:58]2)[CH:54]=[CH:53][C:52]=1[NH2:64]>CN(C=O)C>[C:1]([NH:5][S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]2[N:23]3[C:18]([CH:19]=[N:20][C:21]([NH:64][C:52]4[CH:53]=[CH:54][C:55]([CH:57]5[CH2:58][CH2:59][N:60]([CH3:63])[CH2:61][CH2:62]5)=[CH:56][C:51]=4[O:50][CH3:49])=[N:22]3)=[CH:17][CH:16]=2)[CH:10]=1)(=[O:8])=[O:7])([CH3:3])([CH3:2])[CH3:4]

参加物

6

反応物 4

HCID 81531DiisopropylethylamineHCID 4176748N-Propyl-Methyl Piperidinium Bis(trifluoroMethylsulfonyl)ImideHCID 574160862-Methoxy-4-(1-methylpiperidin-4-yl)anilineHCID 178449976HCID 178449976、化合物

生成物 1

HCID 66711936HCID 66711936、化合物収率 12.4%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

In a 10 mL sealed tube, to N-tert-Butyl-3-(2-hydroxy-pyrrolo[2,1-f][1,2,4]triazin-7-yl)-benzenesulfonamide (100 mg, 0.289 mmol) and N,N-Diisopropylethylamine (0.202 mL, 1.16 mmol) in 3.0 mL of anhydrous DMF was added N-Phenylbis(trifluoromethane-sulfonimide (113 mg, 0.318 mmol). After stirring at room temperature for 30 minutes, 2-Methoxy-4-(1-methyl-piperidin-4-yl)-phenylamine (84 mg, 0.36 mmol) was added. The reaction mixture was heated at 65° C. overnight. The reaction was conc. in vacuo. The reaction mixture was purified via silica gel column chromatography using 500:12:8 DCM:MeOH:7N NH3/MeOH as the eluant. The collected fractions afforded N-tert-Butyl-3-{2-[2-methoxy-4-(1-methyl-piperidin-4-yl)-phenylamino]-pyrrolo[2,1-f][1,2,4]triazin-7-yl}-benzenesulfonamide as a yellow solid (19.66 mg, 11%). MP 189-198° C. LCMS (E/I+) 549.21 (M+H). 1H NMR (DMSO-d6)-9.01 (s, 1H), 8.56 (s, 1H), 8.35 (d, 1H, J=7.88 Hz), 7.99 (d, 1H, J=8.56 Hz), 7.85 (s, 1H), 7.83 (s, 1H), 7.69 (t, 1H, J=7.82 Hz), 7.62 (s, 1H), 7.23 (d, 1H, J=4.72 Hz), 7.01 (d, 1H, J=4.76 Hz), 6.94 (s, 1H), 6.92 (s, 1H), 3.87 (s, 3H), 2.96-2.83 (m, 2H), 2.28-2.17 (s, 3H), 2.10-1.94 (m, 2H), 1.80-1.58 (m, 3H), 1.32-1.21 (m, 1H), 1.12 (s, 9H).

後処理

  1. customIn a 10 mL sealed tube
  2. temperatureThe reaction mixture was heated at 65° C. overnight
  3. customThe reaction mixture was purified via silica gel column chromatography

出典と根拠

ORDレコード
ord-7f0417f201854885867a3dfda2ceb92c
出典データセット
uspto-grants-2013_06
特許番号
US08471005B2

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