Ammonia → 5-phenyl-1H-indole-7-carboxamide

HRID 2267481노트

반응식

HRID 2267481 반응식
[C:1]1([C:7]2[CH:8]=[C:9]3[C:13](=[C:14]([C:16]([OH:18])=O)[CH:15]=2)[NH:12][CH:11]=[CH:10]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.C[N:21](C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1.N>C(Cl)Cl.C1COCC1>[C:1]1([C:7]2[CH:8]=[C:9]3[C:13](=[C:14]([C:16]([NH2:21])=[O:18])[CH:15]=2)[NH:12][CH:11]=[CH:10]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

참가 물질

7

반응물 4

HCID 222AmmoniaHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 545824745-phenyl-1H-indole-7-carboxylic acid

생성물 1

HCID 112070915-phenyl-1H-indole-7-carboxamide

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 5-phenyl-1H-indole-7-carboxylic acid (10.0 g, 42.0 mmol) in a mixture of CH2Cl2 (100 mL) and THF (100 mL) at room temperature, N-(3-Dimethylaminopropy)-N′-ethylcarbodiimide hydrochloride (9.66 g, 50.4 mmol), 1-Hydroxybenzotriazole hydrate (6.81 g, 50.4 mmol) and ammonia (2 M in methanol, 168 mmol, 84 mL) were added. The reaction mixture was stirred at room temperature for 24 hours. All solvent were evaporated and the reaction mixture was partitioned between ethyl acetate (200 mL) and water (200 mL). The organic layer was separated and the aqueous layer was extracted with ethyl acetate (×2). The combined organic phase washed with brine, dried over Mg2SO4 and concentration to give the product which is pure enough for next reaction (10 g, 100%).

후처리

  1. customAll solvent were evaporated
  2. customthe reaction mixture was partitioned between ethyl acetate (200 mL) and water (200 mL)
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with ethyl acetate (×2)
  5. washThe combined organic phase washed with brine
  6. dry with materialdried over Mg2SO4 and concentration
  7. customto give the product which
  8. customis pure enough for next reaction (10 g, 100%)

출처 및 근거

ORD 기록
ord-cc63054342f747f793d32db1e6e63336
출처 데이터셋
uspto-grants-2010_12
특허 번호
US07858796B2

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