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Trifluoroacetic acid → 4-{4-[(3R)-3-Methylmorpholin-4-yl]-6-[1-(S-methylsulfonimidoyl)cyclopropyl]pyrimidin-2-yl}-1H-pyrrolo[2,3-c]pyridine

HRID 1465860
ノート
印刷プレビュー

反応式

HRID 1465860 の反応式
[CH3:1][C@H:2]1[N:7]([C:8]2[CH:13]=[C:12]([C:14]3([S:17]([CH3:20])(=[NH:19])=[O:18])[CH2:16][CH2:15]3)[N:11]=[C:10]([C:21]3[CH:26]=[N:25][CH:24]=[C:23]4[N:27](C(OC(C)(C)C)=O)[CH:28]=[CH:29][C:22]=34)[N:9]=2)[CH2:6][CH2:5][O:4][CH2:3]1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:1][C@@H:2]1[CH2:3][O:4][CH2:5][CH2:6][N:7]1[C:8]1[CH:13]=[C:12]([C:14]2([S:17]([CH3:20])(=[NH:19])=[O:18])[CH2:16][CH2:15]2)[N:11]=[C:10]([C:21]2[CH:26]=[N:25][CH:24]=[C:23]3[NH:27][CH:28]=[CH:29][C:22]=23)[N:9]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 6422Trifluoroacetic acidHCID 86660222Tert-butyl 4-(4-((R)-3-methylmorpholino)-6-(1-(S-methylsulfonimidoyl)cyclopropyl)pyrimidin-2-yl)-1H-pyrrolo[2,3-c]pyridine-1-carboxylate

生成物 1

HCID 547616484-{4-[(3R)-3-Methylmorpholin-4-yl]-6-[1-(S-methylsulfonimidoyl)cyclopropyl]pyrimidin-2-yl}-1H-pyrrolo[2,3-c]pyridine収率 48%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Tert-butyl 4-(4-((R)-3-methylmorpholino)-6-(1-(S-methylsulfonimidoyl)cyclopropyl)pyrimidin-2-yl)-1H-pyrrolo[2,3-c]pyridine-1-carboxylate (0.223 g, 0.44 mmol) was added to TFA (5 ml) and DCM (5.00 ml). The resulting solution was stirred at RT for 1 hour. The reaction mixture was evaporated and the residue was purified by preparative HPLC using decreasingly polar mixtures of water (containing 1% NH3) and MeCN as eluents. Fractions containing the desired compound were evaporated and the residue was triturated with Et2O to give a solid which was collected by filtration and dried under vacuum to afford the title compound (0.086 g, 48%); 1H NMR (400 MHz, DMSO-d6) 1.29 (3H, d), 1.40-1.60 (3H, m), 1.76 (1H, d), 3.11 (3H, s), 3.12-3.21 (1H, m), 3.53 (1H, t), 3.68 (1H, d), 3.80 (2H, d), 4.01 (1H, d), 4.20 (1H, s), 4.58 (1H, s), 6.95 (1H, d), 7.28 (1H, s), 7.71 (1H, s), 8.83 (1H, s), 9.08 (1H, s), 11.75 (1H, s); m/z: (ES+) MH+, 413.16.

後処理

  1. customThe reaction mixture was evaporated
  2. customthe residue was purified by preparative HPLC
  3. additionFractions containing the desired compound
  4. customwere evaporated
  5. customthe residue was triturated with Et2O
  6. customto give a solid which
  7. filtrationwas collected by filtration
  8. customdried under vacuum

出典と根拠

ORDレコード
ord-0a2159e7160b441892188d144378e4f7
出典データセット
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08999997B2

反応ノート

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