Sodium Iodide → 2-{7-[5-(2-Methoxymethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-ylamino]-1,2,4,5-tetrahydro-benzo[d]azepin-3-yl}-N,N-dimethyl-acetamide

HRID 1890001노트

반응식

HRID 1890001 반응식
[CH3:1][O:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[N:15]2[N:16]=[C:17]([NH:19][C:20]3[CH:30]=[CH:29][C:23]4[CH2:24][CH2:25][NH:26][CH2:27][CH2:28][C:22]=4[CH:21]=3)[N:18]=[C:14]2[CH:13]=[CH:12][CH:11]=1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:38][C:39]([N:41]([CH3:43])[CH3:42])=[O:40].[I-].[Na+]>C(#N)C.C(Cl)(Cl)Cl>[CH3:1][O:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[N:15]2[N:16]=[C:17]([NH:19][C:20]3[CH:30]=[CH:29][C:23]4[CH2:24][CH2:25][N:26]([CH2:38][C:39]([N:41]([CH3:43])[CH3:42])=[O:40])[CH2:27][CH2:28][C:22]=4[CH:21]=3)[N:18]=[C:14]2[CH:13]=[CH:12][CH:11]=1

참가 물질

7

반응물 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 758862-chloro-N,N-dimethylacetamideHCID 59612550[5-(2-Methoxymethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-(2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-yl)-amine

생성물 1

HCID 596124882-{7-[5-(2-Methoxymethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-ylamino]-1,2,4,5-tetrahydro-benzo[d]azepin-3-yl}-N,N-dimethyl-acetamide수율 32.1%

시약·촉매·용매 2

HCID 6212Chloroform용매HCID 6342Acetonitrile용매

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온도
70 °C

실험 절차

To a solution of [5-(2-Methoxymethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-(2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-yl)-amine (70.0 mg, 0.18 mmol) in acetonitrile (5 mL) was added potassium carbonate (0.0484 g, 0.350 mmol), 2-chloro-N,N-dimethyl-acetamide (0.0270 mL, 0.263 mmol), followed by sodium iodide (0.0263 g, 0.175 mmol) and the reaction was heated at 70° C. for 2.5 hours and cooled to room temperature. The reaction was diluted with chloroform, washed with water then brine. The organic layer was dried over sodium sulfate, filtered and concentrated. The residue was purified via flash chromatography utilizing an ISCO automated purification apparatus (basic alumina column and 0%→10% methanol in dichloromethane). Product was isolated as a yellow foam (0.028 g, 32%). 1H NMR (400 MHz, CDCl3, δ, ppm): 7.64 (d, J=7.7 Hz, 1H), 7.59-7.42 (m, 5H), 7.27 (m, 1H), 7.23-7.19 (m, 1H), 6.98 (d, J=7.9 Hz, 1H), 6.93 (s, 1H), 6.91-6.87 (m, 1H), 4.35 (br s, 2H), 3.26 (s, 2H), 3.20 (s, 3H), 3.14 (s, 3H), 2.97 (s, 3H), 2.88-2.83 (m, 4H), 2.69-2.63 (m, 4H). MS=485 (MH)+.

후처리

  1. temperaturecooled to room temperature
  2. washwashed with water
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified via flash chromatography
  7. custompurification apparatus (basic alumina column and 0%→10% methanol in dichloromethane)

출처 및 근거

ORD 기록
ord-13f516272cd44ff19c50643ed9c72ade
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08501936B2

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