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Ethanol → HCID 68209970, 화합물

HRID 516696
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HRID 516696 반응식
C(C1[CH:4]=[C:5]([C:16]([NH:18][CH2:19][C:20]2[C:21](=[O:30])[NH:22][C:23]([CH3:29])=[CH:24][C:25]=2[CH2:26][CH2:27][CH3:28])=[O:17])[C:6]2[C:7]([CH3:15])=[CH:8][N:9]([CH:12]([CH3:14])[CH3:13])[C:10]=2[CH:11]=1)#N.[OH-].[K+].C(O)C.CC[O:38][C:39]([CH3:41])=[O:40]>>[CH3:15][C:7]1[C:6]2[C:10](=[CH:11][C:41]([C:39]([OH:38])=[O:40])=[CH:4][C:5]=2[C:16]([NH:18][CH2:19][C:20]2[C:21](=[O:30])[NH:22][C:23]([CH3:29])=[CH:24][C:25]=2[CH2:26][CH2:27][CH3:28])=[O:17])[N:9]([CH:12]([CH3:13])[CH3:14])[CH:8]=1
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참가 물질

5

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HCID 702EthanolHCID 8857Ethyl AcetateHCID 14797Potassium HydroxideHCID 546707286-cyano-3-methyl-1-(1-methylethyl)-N-[(6-methyl-2-oxo-4-propyl-1,2-dihydro-3-pyridinyl)methyl]-1H-indole-4-carboxamide

생성물 1

HCID 68209970HCID 68209970, 화합물수율 64.9%

실험 절차

To a 5 ml microwave vial was added, 6-cyano-3-methyl-1-(1-methylethyl)-N-[(6-methyl-2-oxo-4-propyl-1,2-dihydro-3-pyridinyl)methyl]-1H-indole-4-carboxamide (100 mg, 0.247 mmol), KOH (41.6 mg, 0.742 mmol) was ground and added followed by Ethanol (8 mL) the reaction was microwaved at 145° C. for 22 hr. The reaction was poured onto acidic Ice water (20 mL) and was stirred for 20 min. EtOAc was added and the the mix was stirred an additional 10 min. The layers were separated and the majority of the product was in the EtOAc which was evaporated. The residue was dissolved in MeOH (1 mL) and material was crashed out with ice and was filtered to give product 3-methyl-1-(1-methylethyl)-4-({[(6-methyl-2-oxo-4-propyl-1,2-dihydro-3-pyridinyl)methyl]amino}carbonyl)-1H-indole-6-carboxylic acid (70 mg, 0.160 mmol, 64.9% yield) 1H NMR (400 MHz, DMSO-d6) δ ppm 11.49 (br. s., 1H) 8.18 (s, 1H) 8.10 (s, 1H) 7.53 (d, J=7.58 Hz, 2H) 5.90 (s, 1H) 4.76-4.90 (m, 1H) 4.36 (d, J=4.80 Hz, 2H) 2.55 (br. s., 1H) 2.18 (s, 3H) 2.13 (s, 3H) 1.52-1.61 (m, 2H) 1.44 (d, J=6.57 Hz, 6H) 0.94 (t, J=7.33 Hz, 3H) MS(ES) [M+H]+ 423.8

후처리

  1. additionTo a 5 ml microwave vial was added
  2. additionadded
  3. customwas microwaved at 145° C. for 22 hr
  4. stirringthe the mix was stirred an additional 10 min
  5. customThe layers were separated
  6. customwas evaporated
  7. dissolutionThe residue was dissolved in MeOH (1 mL)
  8. filtrationwas filtered

출처 및 근거

ORD 기록
ord-a9b6c956064348eaabeb5241a50e86c2
출처 데이터셋
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09114141B2

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