Piperidine → 4-[1-(2-aminopyrimidin-4-yl)-2-(2-methoxyethoxy)-1H-1,3-benzodiazol-6-yl]-2-(pyrimidin-2-yl)but-3-yn-2-ol

HRID 1398656

반응식

HRID 1398656 반응식
I[C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[C:8]([O:10][CH2:11][CH2:12][O:13][CH3:14])[N:7]([C:15]3[CH:20]=[CH:19][N:18]=[C:17]([NH2:21])[N:16]=3)[C:6]=2[CH:22]=1.N1CCCCC1.[N:29]1[CH:34]=[CH:33][CH:32]=[N:31][C:30]=1[C:35]([OH:39])([C:37]#[CH:38])[CH3:36]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cu]I>[NH2:21][C:17]1[N:16]=[C:15]([N:7]2[C:6]3[CH:22]=[C:2]([C:38]#[C:37][C:35]([C:30]4[N:29]=[CH:34][CH:33]=[CH:32][N:31]=4)([OH:39])[CH3:36])[CH:3]=[CH:4][C:5]=3[N:9]=[C:8]2[O:10][CH2:11][CH2:12][O:13][CH3:14])[CH:20]=[CH:19][N:18]=1

참가 물질

6

반응물 3

HCID 8082PiperidineHCID 681815974-[6-Iodo-2-(2-methoxyethoxy)-1,3-benzodiazol-1-yl]pyrimidin-2-amineHCID 866695882-(Pyrimidin-2-yl)but-3-yn-2-ol

생성물 1

HCID 681817044-[1-(2-aminopyrimidin-4-yl)-2-(2-methoxyethoxy)-1H-1,3-benzodiazol-6-yl]-2-(pyrimidin-2-yl)but-3-yn-2-ol

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418397HCID 178418397, 화합물촉매

실험 절차

To a pressure tube was added 4-[6-iodo-2-(2-methoxyethoxy)-1H-1,3-benzodiazol-1-yl]pyrimidin-2-amine (70%, 120 mg, 0.2 mmol) followed by piperidine (1.0 mL), tetrakis(triphenylphosphine)palladium(0) (23.61 mg, 0.02 mmol), copper(I) iodide (3.89 mg, 0.02 mmol) and 2-(pyrimidin-2-yl)but-3-yn-2-ol (60.53 mg, 0.41 mmol). The reaction was capped and stirred at RT for 1 h. The reaction mixture was concentrated in vacuo. The crude material was purified by flash column chromatography (1-10% MeOH gradient in DCM), followed by trituration with EtOAc/heptanes/DCM to give the title compound: 1H NMR (500 MHz, DMSO) delta 1.88 (3H, s), 3.92-3.64 (2H, m), 4.84-4.59 (2H, m), 6.13 (1H, s), 6.97 (1H, d, J=5.5 Hz), 7.10 (2H, s), 7.23 (1H, dd, J=8.2, 1.5 Hz), 7.44 (1H, d, J=8.1 Hz), 7.49 (1H, t, J=4.8 Hz), 8.13 (1H, s), 8.39 (1H, d, J=5.5 Hz), 8.89 (2H, d, J=4.9 Hz); LC-MS: m/z=+432.05 (M+H)+.

후처리

  1. customThe reaction was capped
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customThe crude material was purified by flash column chromatography (1-10% MeOH gradient in DCM)

출처 및 근거

ORD 기록
ord-0c3db28da9014945b5ba2c80a6c9a602
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08901313B2

연결된 노트

불러오는 중…