Triethylamine → HCID 178496463、化合物

HRID 724290ノート

反応式

HRID 724290 の反応式
[NH2:1][C@@H:2]1[CH2:7][CH2:6][C@H:5]([NH:8][C:9](=[O:18])[C:10]2[CH:15]=[C:14]([F:16])[CH:13]=[N:12][C:11]=2[Cl:17])[CH2:4][CH2:3]1.C(N(CC)CC)C.[CH3:26][O:27][CH2:28][C:29](O)=[O:30].Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1>CN(C)C=O>[Cl:17][C:11]1[N:12]=[CH:13][C:14]([F:16])=[CH:15][C:10]=1[C:9]([NH:8][C@H:5]1[CH2:6][CH2:7][C@@H:2]([NH:1][C:29](=[O:30])[CH2:28][O:27][CH3:26])[CH2:3][CH2:4]1)=[O:18]

参加物

7

反応物 5

HCID 8471TriethylamineHCID 12251Methoxyacetic AcidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178511677HCID 178511677、化合物

生成物 1

HCID 178496463HCID 178496463、化合物収率 58.8%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

N-(cis-4-Aminocyclohexyl)-2-chloro-5-fluoronicotinamide (837 mg, 2.72 mmol) and triethylamine (1.14 ml, 8.15 mmol) were dissolved in dimethylformamide (20 ml) and 2-methoxy acetic acid (208 μl, 2.72 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (573 mg, 2.99 mmol) and 1-hydroxybenzotriazole (404 mg, 2.99 mmol) were added. The reaction was stirred under nitrogen at room temperature for 18 h then partitioned between water and ethyl acetate. The organic phase was dried over MgSO4 and the solvent was removed under reduced pressure. The residue was purified by flash column chromatography on silica gel eluting using dichloromethane:methanol (96:4 to 91:9) as eluant to give 2-chloro-5-fluoro-N-{cis-4-[(methoxyacetyl)amino]cyclohexyl}nicotinamide (550 mg).

後処理

  1. customthen partitioned between water and ethyl acetate
  2. dry with materialThe organic phase was dried over MgSO4
  3. customthe solvent was removed under reduced pressure
  4. customThe residue was purified by flash column chromatography on silica gel eluting

出典と根拠

ORDレコード
ord-cd707be76ba54c70b01791cd8b48c01f
出典データセット
uspto-grants-2006_11
特許番号
US07141586B2

反応ノート

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