1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 4-(1-(3-Amino-4-methylbenzoyl)azepan-4-yl)benzonitrile

HRID 541218ノート

反応式

HRID 541218 の反応式
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5]([OH:7])=O.[NH:12]1[CH2:18][CH2:17][CH2:16][CH:15]([C:19]2[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[CH:21][CH:20]=2)[CH2:14][CH2:13]1.OC1C2N=NNC=2C=CC=1.C(N=C=NCCCN(C)C)C.C(N(CC)C(C)C)(C)C>C(OCC)(=O)C.CN(C=O)C>[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5]([N:12]1[CH2:18][CH2:17][CH2:16][CH:15]([C:19]2[CH:20]=[CH:21][C:22]([C:23]#[N:24])=[CH:25][CH:26]=2)[CH2:14][CH2:13]1)=[O:7]

参加物

8

反応物 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 755683-Amino-4-methylbenzoic acidHCID 81531DiisopropylethylamineHCID 682889074-(Azepan-4-yl)benzonitrile2 回HCID 178418300HCID 178418300、化合物

生成物 1

HCID 682889154-(1-(3-Amino-4-methylbenzoyl)azepan-4-yl)benzonitrile収率 75%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a 4-mL vial was added 3-amino-4-methylbenzoic acid (27 mg, 0.18 mmol, 1.0 equiv), 4-(azepan-4-yl)benzonitrile (compound 40.4, 40 mg, 0.2 mmol, 1.1 equiv), hydroxybenzotriazole (39 mg of 20 wt % H2O, 0.23 mmol, 1.3 equiv), 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide (44 mg, 0.23 mmol, 1.3 equiv), DMF (1 mL) and N,N-diisopropylethylamine (93 μL, 0.54 mmol, 3.0 equiv). The mixture was stirred at room temperature for 4 hours then diluted into ethyl acetate (10 mL) and washed with brine (10 mL). The aqueous was extracted with ethyl acetate (3 mL) and the combined organics were washed with brine (10 mL), 1 M NaH2PO4 (5 mL) and brine (10 mL). The organics were dried (Na2SO4), filtered and concentrated to obtain the title compound as a brown solid (45 mg, 74%). m/z (ES+) 334 (M+H)+.

後処理

  1. washwashed with brine (10 mL)
  2. extractionThe aqueous was extracted with ethyl acetate (3 mL)
  3. washthe combined organics were washed with brine (10 mL), 1 M NaH2PO4 (5 mL) and brine (10 mL)
  4. dry with materialThe organics were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-32b2a822a30f4affaec8519f8ecc72f2
出典データセット
uspto-grants-2014_10
特許番号
US08871790B2

反応ノート

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