Acetyl chloride → HCID 178474717、化合物

HRID 1508021ノート

反応式

HRID 1508021 の反応式
[C:1](O)(=[O:3])[CH3:2].[NH2:5][C:6]([C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]([C:18]2[NH:19][CH:20]=[C:21]([C:23]#[N:24])[N:22]=2)=[O:17])=[C:11]([C:25]2[CH2:30][CH2:29][CH2:28][CH2:27][CH:26]=2)[CH:10]=1)([CH3:8])[CH3:7].CCN(C(C)C)C(C)C.CN(C1C=CC=CN=1)C.C(Cl)(=O)C>C(Cl)(Cl)Cl.CCOC(C)=O>[C:1]([NH:5][C:6]([C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]([C:18]2[NH:19][CH:20]=[C:21]([C:23]#[N:24])[N:22]=2)=[O:17])=[C:11]([C:25]2[CH2:30][CH2:29][CH2:28][CH2:27][CH:26]=2)[CH:10]=1)([CH3:8])[CH3:7])(=[O:3])[CH3:2]

参加物

7

反応物 4

HCID 6367Acetyl chlorideHCID 218852-DimethylaminopyridineHCID 81531DiisopropylethylamineHCID 178476304HCID 178476304、化合物

生成物 1

HCID 178474717HCID 178474717、化合物収率 16%

試薬・触媒・溶媒 2

HCID 6212Chloroform溶媒2 回HCID 8857Ethyl Acetate溶媒

反応条件

温度
0 °C

実験手順

A mixture of 4-cyano-1H-imidazole-2-carboxylic acid [4-(1-amino-1-methyl-ethyl)-2-cyclohex-1-enyl-phenyl]-amide acetic acid salt (as prepared in the previous step, 50.0 mg, 0.122 mmol) and DIEA (85.0 μL, 0.488 mmol) in 2 mL of CHCl3 was stirred at RT for 5 min before dimethylaminopyridine (DMAP) (4.1 mg, 0.037 mmol) was added. The mixture was cooled to 0° C. and a solution of acetyl chloride (10 μL, 0.15 mmol) in 2 mL of CHCl3 was added dropwise. The reaction was warmed to RT and stirred for 18 h under Ar. The mixture was treated with EtOAc (40 mL), washed with saturated aqueous NaHCO3 (5 mL), brine (10 mL) and dried over Na2SO4. Removal of the solvent under reduced pressure followed by flash chromatography of the residue on silica gel (1-2% MeOH/DCM) gave 7.6 mg (16%) of the title compound as a white solid. 1H-NMR (CD3OD; 400 MHz): δ 8.17 (s, 1H), 8.10 (d, 1H, J=8.6 Hz), 7.99 (s, 1H), 7.27 (dd, 1H, J=8.6, 2.3 Hz), 7.16 (d, 1H, J=2.3 Hz), 5.80 (m, 1H), 2.20-2.32 (m, 4H), 1.94 (s, 3H), 1.74-1.88 (m, 4H), 1.62 (s, 6H). Mass spectrum (ESI, m/z): Calcd. for C22H25N5O2, 392.2 (M+H). found 391.8.

後処理

  1. additionwas added
  2. temperatureThe reaction was warmed to RT
  3. washwashed with saturated aqueous NaHCO3 (5 mL), brine (10 mL)
  4. dry with materialdried over Na2SO4
  5. customRemoval of the solvent under reduced pressure

出典と根拠

ORDレコード
ord-63079a4797444cd083335d13f9d35b4d
出典データセット
uspto-grants-2015_12
特許番号
US09221797B2

反応ノート

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