Potassium Carbonate → 2-((1-(4-amino-1,3,5-triazin-2-yl)-2-methyl-1H-benzo[d]imidazol-6-yl)ethynyl)bicyclo[2.2.1]heptan-2-ol

HRID 1398697노트

반응식

HRID 1398697 반응식
Br[C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[C:8]([CH3:10])[N:7]([C:11]3[N:16]=[CH:15][N:14]=[C:13]([NH2:17])[N:12]=3)[C:6]=2[CH:18]=1.[C:19]([C:21]1([OH:28])[CH2:26][CH:25]2[CH2:27][CH:22]1[CH2:23][CH2:24]2)#[CH:20].C1C=CC(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.[Cu]I>[NH2:17][C:13]1[N:14]=[CH:15][N:16]=[C:11]([N:7]2[C:6]3[CH:18]=[C:2]([C:20]#[C:19][C:21]4([OH:28])[CH2:26][CH:25]5[CH2:27][CH:22]4[CH2:23][CH2:24]5)[CH:3]=[CH:4][C:5]=3[N:9]=[C:8]2[CH3:10])[N:12]=1

참가 물질

8

반응물 4

HCID 11430Potassium CarbonateHCID 812191,3-Bis(diphenylphosphino)propaneHCID 143098132-Ethynylbicyclo(2.2.1)heptan-2-olHCID 681818904-(6-Bromo-2-methyl-benzoimidazol-1-yl)-[1,3,5]triazin-2-ylamine

생성물 1

HCID 681817002-((1-(4-amino-1,3,5-triazin-2-yl)-2-methyl-1H-benzo[d]imidazol-6-yl)ethynyl)bicyclo[2.2.1]heptan-2-ol수율 8%

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 167845palladium(II) acetate촉매HCID 6228Dimethylformamide용매

반응 조건

온도
120 °C

실험 절차

A mixture of 4-(6-bromo-2-methyl-1H-benzo[d]imidazol-1-yl)-1,3,5-triazin-2-amine (200 mg, 0.66 mmol) and 2-ethynylbicyclo[2.2.1]heptan-2-ol (85 mg, 1.3 mmol) in DMF (2.5 mL) was treated with palladium(II) acetate (16 mg, 0.07 mmol), DPPP (58 mg, 0.14 mmol), copper(I) iodide (5 mg, 0.04 mmol) and potassium carbonate (180 mg, 1.3 mmol), then the mixture was heated at 120° C. for 40 min under microwave irradiation. After cooling to RT, the reaction mixture was filtered and the filtrate concentrated in vacuo. Purification of the residue by silica gel column chromatography furnished the title compound (18.5 mg, yield 8%): 1H NMR: (400 MHz, MeOD) delta 1.30-1.47 (m, 4H), 1.56-1.67 (m, 1H), 1.92-2.48 (m, 5H), 2.97 (s, 3H), 7.36 (dd, J=1.6, 8.4 Hz, 1H), 7.53 (d, J=8.4 Hz, 1H), 8.50 (s, 1H), 8.60 (s, 1H); LC-MS: m/z=+361.0 (M+H)+.

후처리

  1. temperatureAfter cooling to RT
  2. filtrationthe reaction mixture was filtered
  3. concentrationthe filtrate concentrated in vacuo
  4. customPurification of the residue by silica gel column chromatography

출처 및 근거

ORD 기록
ord-ce47143e6b564d6d82021c877fba44c4
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08901313B2

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