Hydrochloric Acid → (6-(1,4-Diazepan-1-yl)pyridin-2-yl)(2-amino-5-bromopyridin-3-yl)methanone

HRID 1929361ノート

反応式

HRID 1929361 の反応式
[NH2:1][C:2]1[N:29]=[CH:28][C:27]([Br:30])=[CH:26][C:3]=1[C:4]([C:6]1[N:11]=[C:10]([N:12]2[CH2:18][CH2:17][CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14][CH2:13]2)[CH:9]=[CH:8][CH:7]=1)=[O:5].Cl>O1CCOCC1>[N:12]1([C:10]2[N:11]=[C:6]([C:4]([C:3]3[C:2]([NH2:1])=[N:29][CH:28]=[C:27]([Br:30])[CH:26]=3)=[O:5])[CH:7]=[CH:8][CH:9]=2)[CH2:18][CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1

参加物

4

反応物 2

HCID 313Hydrochloric AcidHCID 57690601Tert-butyl 4-(6-(2-amino-5-bromonicotinoyl)pyridin-2-yl)-1,4-diazepane-1-carboxylate

生成物 1

HCID 24871523(6-(1,4-Diazepan-1-yl)pyridin-2-yl)(2-amino-5-bromopyridin-3-yl)methanone収率 36%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒2 回

実験手順

To a suspension of tert-butyl 4-(6-(2-amino-5-bromonicotinoyl)pyridin-2-yl)-1,4-diazepane-1-carboxylate (0.050 g, 0.10 mmol) in 1,4-dioxane (2 ml) was added 4 M HCl in 1,4-dioxane (1 ml) and the resulting mixture was stirred at room temperature for 5 hours. Reaction mixture was then concentrated to dryness in vacuo and the crude product purified by prep-LCMS, then freeze-dried to leave title compound as a yellow solid (13.5 mg, 36%). 1H NMR (DMSO-d6 1.84-1.76 (2H, m), 2.08 (1H, s), 2.71-2.68 (1H, m), 2.89-2.86 (1H, m), 3.72-3.28 (6H, masked signal), 6.89 (10.5H, d), 6.95 (0.5H, d), 7.05 (0.5H, d), 7.10 (0.5H, d), 7.74-7.68 (1H, m), 7.81 (2H, br s), 8.31 (1H, d), 8.54 (1H, d). ES+ 378.15.

後処理

  1. customReaction mixture
  2. concentrationwas then concentrated to dryness in vacuo
  3. customthe crude product purified by prep-LCMS
  4. customfreeze-dried

出典と根拠

ORDレコード
ord-48cf2008c5b54d67822fea91de675ff1
出典データセット
uspto-grants-2012_05
特許番号
US08188071B2

反応ノート

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