Triethylamine → 1,1-Dimethylethyl 9-(5-{5-chloro-6-[(1-methylethyl)oxy]-3-pyridinyl}-1,2,4-oxadiazol-3-yl)-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate

HRID 1514245ノート

反応式

HRID 1514245 の反応式
C(N(CC)CC)C.[Cl:8][C:9]1[CH:10]=[C:11]([C:19]([OH:21])=O)[CH:12]=[N:13][C:14]=1[O:15][CH:16]([CH3:18])[CH3:17].O.OC1C2N=NNC=2C=CC=1.Cl.CN(C)CCCN=C=NCC.O[NH:46][C:47](=[NH:66])[C:48]1[C:58]2[O:57][CH2:56][CH2:55][N:54]([C:59]([O:61][C:62]([CH3:65])([CH3:64])[CH3:63])=[O:60])[CH2:53][C:52]=2[CH:51]=[CH:50][CH:49]=1>CN(C)C=O.C(OCC)(=O)C>[Cl:8][C:9]1[CH:10]=[C:11]([C:19]2[O:21][N:46]=[C:47]([C:48]3[C:58]4[O:57][CH2:56][CH2:55][N:54]([C:59]([O:61][C:62]([CH3:65])([CH3:64])[CH3:63])=[O:60])[CH2:53][C:52]=4[CH:51]=[CH:50][CH:49]=3)[N:66]=2)[CH:12]=[N:13][C:14]=1[O:15][CH:16]([CH3:17])[CH3:18]

参加物

8

反応物 5

HCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 180705825-Chloro-6-isopropoxynicotinic acidHCID 178452412HCID 178452412、化合物HCID 178526939HCID 178526939、化合物

生成物 1

HCID 594034701,1-Dimethylethyl 9-(5-{5-chloro-6-[(1-methylethyl)oxy]-3-pyridinyl}-1,2,4-oxadiazol-3-yl)-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate収率 57%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
60 °C

実験手順

Triethylamine (0.281 ml, 2.02 mmol) was added to a stirred solution of 5-chloro-6-[(1-methylethyl)oxy]-3-pyridinecarboxylic acid (may be prepared as described in WO9702244; 217 mg, 1.01 mmol) in N,N-dimethylformamide (20 ml) followed by hydroxybenzotriazole hydrate (185 mg, 1.21 mmol) then 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (232 mg, 1.21 mmol) and lastly 1,1-dimethylethyl 9-[(hydroxyamino)(imino)methyl]-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate (Preparation 65) (310 mg, 1.009 mmol). The reaction mixture was heated to 60° C. for 48 hours, then allowed to cool before diluting with ethyl acetate and washing with water. The organic phase was dried and evaporated. Purification of the residue by column chromatography, eluting with 15-25% ethyl acetate in cyclohexane to give the title compound as an amber coloured gum (280 mg).

後処理

  1. temperatureto cool
  2. washwashing with water
  3. customThe organic phase was dried
  4. customevaporated
  5. customPurification of the residue by column chromatography
  6. washeluting with 15-25% ethyl acetate in cyclohexane

出典と根拠

ORDレコード
ord-f8572d34488d45638b8d9da298115f82
出典データセット
uspto-grants-2012_07
特許番号
US08222245B2

反応ノート

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