Triethylamine → 2-chloro-11-fluoro-6H-pyrido[2',3':5,6][1,3]oxazino[3,4-a]indole-6-carboxamide

HRID 1776860ノート

反応式

HRID 1776860 の反応式
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:18][CH:17]([C:19](O)=[O:20])[N:8]3[C:9]4[CH:10]=[CH:11][CH:12]=[C:13]([F:16])[C:14]=4[CH:15]=[C:7]3[C:6]=2[N:22]=1.[NH4+].[Cl-].C1C=CC2N(O)N=[N:31]C=2C=1.CCN=C=NCCCN(C)C.C(N(CC)CC)C>CN(C=O)C.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:18][CH:17]([C:19]([NH2:31])=[O:20])[N:8]3[C:9]4[CH:10]=[CH:11][CH:12]=[C:13]([F:16])[C:14]=4[CH:15]=[C:7]3[C:6]=2[N:22]=1

参加物

8

反応物 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 25517Ammonium ChlorideHCID 757711-HydroxybenzotriazoleHCID 867282632-chloro-11-fluoro-6H-pyrido[2',3':5,6][1,3]oxazino[3,4-a]indole-6-carboxylic acid

生成物 1

HCID 867282642-chloro-11-fluoro-6H-pyrido[2',3':5,6][1,3]oxazino[3,4-a]indole-6-carboxamide収率 33.3%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

A mixture of 2-chloro-11-fluoro-6H-pyrido[2′,3′:5,6][1,3]oxazino[3,4-a]indole-6-carboxylic acid (60 mg, 0.19 mmol), NH4Cl (20 mg, 0.38 mmol), HOBT (38 mg, 0.28 mmol), EDCI (54 mg, 0.28 mmol) and triethylamine (76 mg, 0.75 mmol) in DMF (1 mL) was stirred at room temperature overnight under N2 atmosphere. The mixture was then diluted with water (30 mL) and extracted with EtOAc (20 mL×3). The organic layer was washed with brine (30 mL×3), dried over Na2SO4 and concentrated in vacuo. The resulting residue was purified using column chromatography (dichloromethane:MeOH=30:1) to provide 2-chloro-11-fluoro-6H-pyrido[2′,3′:5,6][1,3]oxazino[3,4-a]indole-6-carboxamide (20 mg, yield: 33.3%). 1H-NMR (Methanol-d4, 400 MHz) δ 7.54 (d, J=8.4 Hz, 1H), 7.28˜7.31 (m, 2H), 7.20˜7.24 (m, 2H), 6.90 (s, 1H), 6.82˜6.84 (m, 1H). MS (M+H)+: 318.

後処理

  1. extractionextracted with EtOAc (20 mL×3)
  2. washThe organic layer was washed with brine (30 mL×3)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe resulting residue was purified

出典と根拠

ORDレコード
ord-4d27c1944c9f400592e3ff6ba893aca9
出典データセット
uspto-grants-2016_02
特許番号
US09265773B2

反応ノート

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