Dimethylformamide → 2-(5-Methoxy-2-methyl-1h-indol-3-yl)acetamide

HRID 381400

反応式

HRID 381400 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([CH3:12])=[C:6]2[CH2:13][C:14]([OH:16])=O.CC[N:19]=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[Cl-].[NH4+].CN(C=O)C>O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([CH3:12])=[C:6]2[CH2:13][C:14]([NH2:19])=[O:16]

参加物

8

反応物 6

HCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 757711-HydroxybenzotriazoleHCID 761515-Methoxy-2-methylindole-3-acetic acidHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

生成物 1

HCID 2441462-(5-Methoxy-2-methyl-1h-indol-3-yl)acetamide収率 64%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A reaction mixture containing Compound 1 (880 mg, 4.02 mmol), EDCl (1.16 g,6.04 mmol), HOBt (816 mg,6.04 mmol), DIPEA (2.8 mL, 16.08 mmol), ammonium chloride (430 mg, 8.04 mmol) in anhydrous DMF 16 mL (4 mL DMF/1 mmol) was stirred at rt for 5 hours. The reaction was diluted with water and extracted with EtOAc (3×10 mL). The combined EtOAc extracts were washed with saturated NaHCO3 (2×10 mL), water, dried (MgSO4), filtered, and the solvent concentrated in vacuo till a minimum volume of EtOAc remained. Upon cooling, the desired primary amide crystallized out as a white crystalline solid, in 64% yield. mp=146-148° C. t is noted that Shaw, “The Synthesis of Tryptamines Related to Seratonin”, Vol. 77, J. Amer. Chem. Soc., pp. 4319-4324 (1955) reported the mp=147-150° C. 1H NMR (DMSO-d6) δ 10.56 (s, 1 H, NH), 7.34 (bs, 1 H, CONH), 6.96-7.22 (m, 1 H, ArH), 6.81 (s, 1 H, ArH), 6.74 (bs, 1 H, CONH), 6.58-6.62 (m, 1 H, ArH), 3.78 (s, 3 H, CH3), 3.34 (s, 2 H, CH2), 2.29 (s, 3 H, CH3). ESI-CID 219 (MH+), m/z 187, 174, 148.

後処理

  1. extractionextracted with EtOAc (3×10 mL)
  2. washThe combined EtOAc extracts were washed with saturated NaHCO3 (2×10 mL), water
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationthe solvent concentrated in vacuo till a minimum volume of EtOAc
  6. temperatureUpon cooling
  7. customthe desired primary amide crystallized out as a white crystalline solid, in 64% yield
  8. customThe Synthesis of Tryptamines

出典と根拠

ORDレコード
ord-9cda3f52a85642a796926de967d07843
出典データセット
uspto-grants-2001_10
特許番号
US06306890B1

関連ノート

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