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Trifluoroacetic acid → 4-(6-(2H-1,2,3-triazol-2-yl)pyridin-2-ylamino)-6-((1R,2S)-2-aminocyclohexylamino)pyridazine-3-carboxamide

HRID 1396412
ノート
印刷プレビュー

反応式

HRID 1396412 の反応式
[N:1]1[N:2]([C:6]2[N:11]=[C:10]([NH:12][C:13]3[CH:14]=[C:15]([NH:22][C@@H:23]4[CH2:28][CH2:27][CH2:26][CH2:25][C@@H:24]4[NH:29]C(=O)OC(C)(C)C)[N:16]=[N:17][C:18]=3[C:19](=[O:21])[NH2:20])[CH:9]=[CH:8][CH:7]=2)[N:3]=[CH:4][CH:5]=1.FC(F)(F)C(O)=O>ClCCl.[OH-].[Na+]>[N:1]1[N:2]([C:6]2[N:11]=[C:10]([NH:12][C:13]3[CH:14]=[C:15]([NH:22][C@@H:23]4[CH2:28][CH2:27][CH2:26][CH2:25][C@@H:24]4[NH2:29])[N:16]=[N:17][C:18]=3[C:19]([NH2:20])=[O:21])[CH:9]=[CH:8][CH:7]=2)[N:3]=[CH:4][CH:5]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 6422Trifluoroacetic acidHCID 86689762tert-butyl (1S,2R)-2-(5-(6-(2H-1,2,3-triazol-2-yl)pyridin-2-ylamino)-6-carbamoylpyridazin-3-ylamino)cyclohexylcarbamate

生成物 1

HCID 716269734-(6-(2H-1,2,3-triazol-2-yl)pyridin-2-ylamino)-6-((1R,2S)-2-aminocyclohexylamino)pyridazine-3-carboxamide収率 7%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒2 回
HCID 14798
Sodium Hydroxide
溶媒

実験手順

To a solution of tert-butyl (1S,2R)-2-(5-(6-(2H-1,2,3-triazol-2-yl)pyridin-2-ylamino)-6-carbamoylpyridazin-3-ylamino)cyclohexylcarbamate (79 mg, 160 μmol) in dichloromethane (2.5 mL) was added trifluoroacetic acid (364 mg, 246 μL, 3.19 mmol) and the mixture stirred at room temperature for 16 h. The mixture was diluted with dichloromethane and 1 N NaOH (2 mL), and then washed with NaHCO3 and brine. The organic layer was dried over MgSO4, then filtered and concentrated in vacuo. The mixture was dissolved in ethanol and concentrated (3×). The residue obtained was triturated with ether and finally filtered to give 4-(6-(2H-1,2,3-triazol-2-yl)pyridin-2-ylamino)-6-((1R,2S)-2-aminocyclohexylamino)pyridazine-3-carboxamide (5 mg, 10.8 μmol, 7%) as a light brown solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.12 (s, 1H), 8.46 (s, 1H), 8.38 (s, 2H), 7.99 (t, J=8.1 Hz, 1H), 7.80 (s, 1H), 7.62 (d, J=8.1 Hz, 1H), 7.11 (d, J=8.2 Hz, 1H), 6.94 (s., 1H), 1.35-1.85 (m, 8H), 1.46 (m, 2H); MS (EI/CI) m/z: 395.1 [M+H].

後処理

  1. washwashed with NaHCO3 and brine
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. dissolutionThe mixture was dissolved in ethanol
  6. concentrationconcentrated (3×)
  7. customThe residue obtained
  8. customwas triturated with ether
  9. filtrationfinally filtered

出典と根拠

ORDレコード
ord-8a87bdf42dd34ccaa9a94293ecb1884c
出典データセット
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08901124B2

反応ノート

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