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Diisopropylethylamine → 4-Amino-6-[1-(3-pyridin-2-yl-imidazo[1,2-b]pyridazin-2-yl)-ethyl amino]-pyrimidine-5-carbonitrile

HRID 2036659
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HRID 2036659 반응식
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[N:11]2[N:12]=[CH:13][CH:14]=[CH:15][C:10]2=[N:9][C:8]=1[CH:16]([NH2:18])[CH3:17].[NH2:19][C:20]1[C:25]([C:26]#[N:27])=[C:24](Cl)[N:23]=[CH:22][N:21]=1.CCN(C(C)C)C(C)C>C(O)CCC>[NH2:19][C:20]1[C:25]([C:26]#[N:27])=[C:24]([NH:18][CH:16]([C:8]2[N:9]=[C:10]3[CH:15]=[CH:14][CH:13]=[N:12][N:11]3[C:7]=2[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)[CH3:17])[N:23]=[CH:22][N:21]=1
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참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 122782624-Amino-6-chloropyrimidine-5-carbonitrileHCID 674336131-(3-Pyridin-2-yl-imidazo[1,2-b]pyridazin-2-yl)-ethylamine

생성물 1

HCID 674322994-Amino-6-[1-(3-pyridin-2-yl-imidazo[1,2-b]pyridazin-2-yl)-ethyl amino]-pyrimidine-5-carbonitrile

시약·촉매·용매 1

HCID 2631-Butanol용매

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온도
110 °C

실험 절차

To a mixture of 1-(3-pyridin-2-yl-imidazo[1,2-b]pyridazin-2-yl)-ethylamine (450 mg, 2.09 mmol) and 4-amino-6-chloro-pyrimidine-5-carbonitrile (325 mg, 2.09 mmol) in n-butanol (8 mL) was added DIEA (0.6 mL, 3.01 mmol) at rt. The reaction mixture was stirred at 110° C. overnight. The mixture was concentrated in vacuo. The residue was purified by column chromatography using silica gel (100-200 mesh) and 0-60% acetone in hexane to provide 4-amino-6-[1-(3-pyridin-2-yl-imidazo[1,2-b]pyridazin-2-yl)-ethyl amino]-pyrimidine-5-carbonitrile: 1H NMR (400 MHz, DMSO-d6) δ 1.272 (d, J=6.4 Hz, 3H), 6.047-6.118 (m, 1H), 7.375 (br s, 2H), 7.446-7.477 (m, 2H), 8.022-8.060 (m, 2H), 8.230-8.280 (m, 1H), 8.400-8.490 (m, 2H), 8.727 (s, 1H), 8.878 (s, 1H). LC-MS (ESI) m/z 358.2 [M+H]+.

후처리

  1. concentrationThe mixture was concentrated in vacuo
  2. customThe residue was purified by column chromatography

출처 및 근거

ORD 기록
ord-ca9752f3808741698812312be77cd986
출처 데이터셋
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08575183B2

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