Trifluoroacetic acid → HCID 178460032、化合物

HRID 577690ノート

反応式

HRID 577690 の反応式
[CH3:1][N:2]1[CH2:6][CH2:5][CH:4]([N:7]2[CH:11]=[C:10]([NH:12][C:13]3[N:21]=[C:20]4[C:16]([N:17]=[CH:18][N:19]4COCC[Si](C)(C)C)=[C:15]([O:30][C:31]4[CH:32]=[C:33]([NH:37][C:38](=[O:41])[CH:39]=[CH2:40])[CH:34]=[CH:35][CH:36]=4)[N:14]=3)[CH:9]=[N:8]2)[CH2:3]1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:1][N:2]1[CH2:6][CH2:5][CH:4]([N:7]2[CH:11]=[C:10]([NH:12][C:13]3[N:21]=[C:20]4[C:16]([N:17]=[CH:18][NH:19]4)=[C:15]([O:30][C:31]4[CH:32]=[C:33]([NH:37][C:38](=[O:41])[CH:39]=[CH2:40])[CH:34]=[CH:35][CH:36]=4)[N:14]=3)[CH:9]=[N:8]2)[CH2:3]1

参加物

4

反応物 2

HCID 6422Trifluoroacetic acidHCID 86679632HCID 86679632、化合物

生成物 1

HCID 178460032HCID 178460032、化合物収率 10%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a mixture of N-{3-[(2-{[1-(1-methylpyrrolidin-3-yl)-1H-pyrazol-4-yl]amino}-9-{[2-(trimethylsilyl)ethoxy]methyl}-9H-purin-6-yl)oxy]phenyl}prop-2-enamide (271 mg, 0.471 mmol) in DCM (5.89 mL) was added TFA (1.81 mL, 23.6 mmol). The resulting solution was stirred at rt overnight, then concentrated and dried under vacuum. The resulting residue was taken up in water and neutralized with NaHCO3 to get a slightly sticky suspension. The solid was filtered off, washed with water, dried, and collected to give the crude product, which was purified by SFC to afford the title compound (21 mg, 10 yield) as a lyophilized solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.80 (br. s., 1H) 10.37 (br. s., 1H) 9.20 (br. s., 1H) 8.01-8.11 (m, 1H) 7.61-7.78 (m, 1H) 7.48 (br. s., 1H) 7.37 (d, J=6.32 Hz, 1H) 7.03 (d, J=7.33 Hz, 2H) 6.36-6.59 (m, 1H) 6.20-6.34 (m, 1H) 5.77 (dd, J=10.23, 1.89 Hz, 1H) 4.57 (br. s., 1H) 3.99-4.27 (m, 1H) 3.65-3.94 (m, 3H) 3.00 (br. s., 2H) 2.79 (m, J=15.66 Hz, 1H) 2.00 (br. s., 1H) 1.23 (s, 1H). m/z (APCI+) for C22H23N9O2 446.05 (M+H)+.

後処理

  1. concentrationconcentrated
  2. customdried under vacuum
  3. customto get a slightly sticky suspension
  4. filtrationThe solid was filtered off
  5. washwashed with water
  6. customdried
  7. customcollected
  8. customto give the crude product, which
  9. customwas purified by SFC

出典と根拠

ORDレコード
ord-f17d8639c0a248ba8eed55692627ffa0
出典データセット
uspto-grants-2015_05
特許番号
US09040547B2

反応ノート

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