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Triethylamine → Tert-butyl [2-({6-cyano-5-[(4,6-dimethylpyridin-2-yl)amino]pyridin-3-yl}sulfamoyl)ethyl]carbamate

HRID 1504892
ノート
印刷プレビュー

反応式

HRID 1504892 の反応式
[NH2:1][C:2]1[CH:3]=[C:4]([NH:10][C:11]2[CH:16]=[C:15]([CH3:17])[CH:14]=[C:13]([CH3:18])[N:12]=2)[C:5]([C:8]#[N:9])=[N:6][CH:7]=1.C(N(CC)CC)C.Cl[S:27]([CH2:30][CH2:31][NH:32][C:33](=[O:39])[O:34][C:35]([CH3:38])([CH3:37])[CH3:36])(=[O:29])=[O:28]>C(Cl)Cl.C(OCC)(=O)C.C(=O)(O)[O-].[Na+]>[C:8]([C:5]1[N:6]=[CH:7][C:2]([NH:1][S:27]([CH2:30][CH2:31][NH:32][C:33](=[O:39])[O:34][C:35]([CH3:37])([CH3:36])[CH3:38])(=[O:29])=[O:28])=[CH:3][C:4]=1[NH:10][C:11]1[CH:16]=[C:15]([CH3:17])[CH:14]=[C:13]([CH3:18])[N:12]=1)#[N:9]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 3

HCID 8471TriethylamineHCID 17750969tert-butyl N-[2-(chlorosulfonyl)ethyl]carbamate2 回HCID 867316535-Amino-3-[(4,6-dimethylpyridin-2-yl)amino]pyridine-2-carbonitrile

生成物 1

HCID 131734337Tert-butyl [2-({6-cyano-5-[(4,6-dimethylpyridin-2-yl)amino]pyridin-3-yl}sulfamoyl)ethyl]carbamate

試薬・触媒・溶媒 3

HCID 6344Dichloromethane
溶媒
HCID 8857Ethyl Acetate溶媒
HCID 516892Sodium Bicarbonate溶媒

実験手順

To a solution of 5-amino-3-[(4,6-dimethylpyridin-2-yl)amino]pyridine-2-carbonitrile (PrepEx 1.8) (150 mg, 0.63 mmol) in DCM (5 mL) was added triethylamine (0.26 mL, 1.88 mmol) followed by the dropwise addition of tert-butyl [2-(chlorosulfonyl)ethyl]carbamate (25% w/w in DCM, 920 mg, 0.94 mmol). The reaction mixture was stirred for 3 hours at room temperature. Additional tert-butyl [2-(chlorosulfonyl)ethyl]carbamate (25% w/w in DCM, 920 mg, 0.94 mmol) was added and the reaction mixture was stirred for 16 hours. The reaction mixture was diluted with ethyl acetate and saturated aqueous sodium bicarbonate. The organics were separated, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by chromatography on silica gel to afford tert-butyl [2-({6-cyano-5-[(4,6-dimethylpyridin-2-yl)amino]pyridin-3-yl}sulfamoyl)ethyl]carbamate. MS ESI calc'd. for C20H27N6O4S [M+H]+ 447. found 447. 1H NMR (500 MHz, DMSO-d6) δ 10.70 (s, 1H), 9.19 (s, 1H), 8.50 (s, 1H), 8.01 (s, 1H), 6.86 (t, J=5.5 Hz, 1H), 6.73 (s, 1H), 6.65 (s, 1H), 3.41 (t, J=6.7 Hz, 2H), 3.32-3.29 (m, 2H), 2.31 (s, 3H), 2.22 (s, 3H), 1.30 (s, 9H).

後処理

  1. stirringthe reaction mixture was stirred for 16 hours
  2. customThe organics were separated
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by chromatography on silica gel

出典と根拠

ORDレコード
ord-a25410cd57f94c038dcd66a99bf96f80
出典データセット
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09216173B2

反応ノート

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