Acetyl chloride → N-(5-(4-Acetyl-1-piperazinyl)-2-pyridinyl)-9-cyclopentyl-9H-pyrido[4',3':4,5]-pyrrolo[2,3-d]pyrimidin-2-amine

HRID 875959노트

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HRID 875959 반응식
[CH:1]1([N:6]2[C:10]3[N:11]=[C:12]([NH:15][C:16]4[CH:21]=[CH:20][C:19]([N:22]5[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]5)=[CH:18][N:17]=4)[N:13]=[CH:14][C:9]=3[C:8]3[CH:28]=[CH:29][N:30]=[CH:31][C:7]2=3)[CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)C(C)C)(C)C.[C:41](Cl)(=[O:43])[CH3:42]>CN(C=O)C>[C:41]([N:25]1[CH2:26][CH2:27][N:22]([C:19]2[CH:20]=[CH:21][C:16]([NH:15][C:12]3[N:13]=[CH:14][C:9]4[C:8]5[CH:28]=[CH:29][N:30]=[CH:31][C:7]=5[N:6]([CH:1]5[CH2:2][CH2:3][CH2:4][CH2:5]5)[C:10]=4[N:11]=3)=[N:17][CH:18]=2)[CH2:23][CH2:24]1)(=[O:43])[CH3:42]

참가 물질

5

반응물 3

HCID 6367Acetyl chlorideHCID 81531DiisopropylethylamineHCID 441325859-Cyclopentyl-N-(5-Piperazin-1-Ylpyridin-2-Yl)pyrido[4,5]pyrrolo[1,2-D]pyrimidin-2-Amine

생성물 1

HCID 58300101N-(5-(4-Acetyl-1-piperazinyl)-2-pyridinyl)-9-cyclopentyl-9H-pyrido[4',3':4,5]-pyrrolo[2,3-d]pyrimidin-2-amine수율 74.5%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

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온도
0 °C

실험 절차

To a solution of compound 7 (207 mg, 0.50 mmol) in DMF (5 mL) were added N,N-diisopropylethylamine (174 uL, 1.0 mmol) and acetyl chloride (43 uL, 0.60 mmol) in DMF (2 mL) at 0° C. and the resulted mixture was stirred at 0° C. for 1 hr. The reaction mixture was concentrated and the residue was washed with water (sonicated) and the solid was collected by filtration, dried under high vacuum to give compound 186 (170 mg, 74% yield) as a light yellow solid. 1H NMR (500 MHz, DMSO-d6) δ 9.82 (1H, s), 9.27 (1H, s), 9.01 (1H, s), 8.44 (1 H, d, J=5 Hz), 8.21 (1H, d, J=10 Hz), 8.07 (1H, d, J=2 Hz), 8.04 (1H, d, J=5 Hz), 7.52 (1H, dd, J=10 Hz, J=2 Hz), 5.37 (1H, p, J=10 Hz), 3.61 (4H, q, J=5 Hz), 3.17 (2H, t, J=5 Hz), 3.10 (2H, t, J=5 Hz), (3H, s), 2.40 (2H, m), 2.08 (4H, m), 2.06 (3H, s), 1.78 (2H, m) ppm; LCMS-ESI (POS), M/Z, M+1: Found 456.1, Calculated 456.2.

후처리

  1. concentrationThe reaction mixture was concentrated
  2. washthe residue was washed with water (sonicated)
  3. filtrationthe solid was collected by filtration
  4. customdried under high vacuum

출처 및 근거

ORD 기록
ord-bc8f166d1c6a48f1a75c7e7f5e0622cc
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08980903B2

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