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1,2-Dichloroethane → 5-bromo-N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-3-(1-methylethyl)-1H-indole-7-carboxamide

HRID 1616811
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HRID 1616811 반응식
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([C:11]([OH:13])=O)[CH:10]=1)[NH:7][CH:6]=[C:5]2[CH:14]([CH3:16])[CH3:15].[NH2:17][CH2:18][C:19]1[C:20](=[O:27])[NH:21][C:22]([CH3:26])=[CH:23][C:24]=1[CH3:25].C1C=NC2N(O)N=NC=2C=1.CN1CCOCC1.C(Cl)CCl>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([C:11]([NH:17][CH2:18][C:19]3[C:20](=[O:27])[NH:21][C:22]([CH3:26])=[CH:23][C:24]=3[CH3:25])=[O:13])[CH:10]=1)[NH:7][CH:6]=[C:5]2[CH:14]([CH3:16])[CH3:15]
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참가 물질

7

반응물 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 181649HOAtHCID 70638443-(Aminomethyl)-4,6-dimethyl-1,2-dihydropyridin-2-oneHCID 678183425-Bromo-3-isopropyl-1H-indole-7-carboxylic acid

생성물 1

HCID 678124415-bromo-N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-3-(1-methylethyl)-1H-indole-7-carboxamide
수율 97%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a stirred suspension of 5-bromo-3-(1-methylethyl)-1H-indole-7-carboxylic acid (400 mg, 1.418 mmol), 3-(aminomethyl)-4,6-dimethyl-2(1H)-pyridinone (300 mg, 1.590 mmol) and HOAt (220 mg, 1.616 mmol) in DMF (15 mL) was added N-methylmorpholine (180 μL, 1.637 mmol) and EDC free base (330 mg, 2.127 mmol). The reaction was stirred for 18 h at RT. LCMS showed that the reaction was complete. The reaction was evaporated to near dryness under vacuum. Water (˜15 mL) was added and the solids which precipitated out were triturated, filtered and dried under vacuum to give 5-bromo-N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-3-(1-methylethyl)-1H-indole-7-carboxamide (571 mg, 1.372 mmol, 97% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 11.52 (br. s., 1H), 11.03 (br. s., 1H), 8.58 (t, J=4.55 Hz, 1H), 7.85 (d, J=1.26 Hz, 1H), 7.82 (s, 1H), 7.12 (d, J=2.02 Hz, 1H), 5.89 (s, 1H), 4.35 (d, J=4.55 Hz, 2H), 3.13 (ddd, J=6.57, 6.69, 13.52 Hz, 1H), 2.20 (s, 3H), 2.13 (s, 3H), 1.27 (d, J=6.82 Hz, 6H). MS (ES) [M+H]+ 415.9, 418.0.

후처리

  1. customThe reaction was evaporated
  2. additionWater (˜15 mL) was added
  3. customthe solids which precipitated out
  4. customwere triturated
  5. filtrationfiltered
  6. customdried under vacuum

출처 및 근거

ORD 기록
ord-40710d8b2dae4b279755b89bad746456
출처 데이터셋
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08765792B2

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