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Heptane → N-Methyl-4-{4-phenyl-1-[1-(pyrimidin-2-ylmethyl)piperidin-4-yl]-1H-imidazol-5-yl}pyrimidin-2-amine

HRID 1896664
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HRID 1896664 반응식
[CH3:1][NH:2][C:3]1[N:8]=[C:7]([C:9]2[N:13]([CH:14]3[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]3)[CH:12]=[N:11][C:10]=2[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:6]=[CH:5][N:4]=1.Cl[CH2:27][C:28]1[N:33]=[CH:32][CH:31]=[CH:30][N:29]=1.FC1C=CC(C2N=CN(C3CCN(CC4N=CC=CN=4)CC3)C=2C2C=CN=C(N)N=2)=CC=1.CCCCCCC>ClCCl.O>[CH3:1][NH:2][C:3]1[N:8]=[C:7]([C:9]2[N:13]([CH:14]3[CH2:15][CH2:16][N:17]([CH2:27][C:28]4[N:33]=[CH:32][CH:31]=[CH:30][N:29]=4)[CH2:18][CH2:19]3)[CH:12]=[N:11][C:10]=2[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:6]=[CH:5][N:4]=1
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참가 물질

7

반응물 4

HCID 8900HeptaneHCID 128773712-(Chloromethyl)pyrimidineHCID 574617294-{4-(4-Fluorophenyl)-1-[1-(pyrimidin-2-ylmethyl)piperidin-4-yl]-1H-imidazol-5-yl}pyrimidin-2-amineHCID 58235131HCID 58235131, 화합물

생성물 1

HCID 58235122N-Methyl-4-{4-phenyl-1-[1-(pyrimidin-2-ylmethyl)piperidin-4-yl]-1H-imidazol-5-yl}pyrimidin-2-amine

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매2회

실험 절차

The title product was prepared by reaction of N-methyl-4-(4-phenyl-1-piperidin-4-yl-1H-imidazol-5-yl)pyrimidin-2-amine (C26) with 2-(chloromethyl)-pyrimidine according to the general procedure for the synthesis of 4-{4-(4-fluorophenyl)-1-[1-(pyrimidin-2-ylmethyl)piperidin-4-yl]-1H-imidazol-5-yl}pyrimidin-2-amine (3) in Example 3. In this case, after the reaction cooled to room temperature, it was diluted with dichloromethane (20 mL) and water (2 mL). The organic layer was dried over magnesium sulfate, filtered and concentrated in vacuo to provide a light yellow solid, which was dissolved in a small volume of dichloromethane. Addition of heptane caused a solid to precipitate; this mixture was stirred for 30 minutes and then the solid was collected by filtration, washed with heptane and washed with diethyl ether to provide the product as a light yellow solid. Yield: 106 mg, 0.248 mmol, 34%. APCI m/z 427.1 (M+1). 1H NMR (400 MHz, CD3OD) δ 2.12-2.17 (m, 4H), 2.29-2.36 (m, 2H), 2.97 (s, 3H), 3.11 (br d, J=12 Hz, 2H), 3.85 (s, 2H), 4.74 (br s, 1H), 6.34 (d, J=5.1 Hz, 1H), 7.29-7.35 (m, 3H), 7.38-7.43 (m, 3H), 8.06 (s, 1H), 8.09 (br d, J=5 Hz, 1H), 8.80 (d, J=4.9 Hz, 2H).

후처리

  1. dry with materialThe organic layer was dried over magnesium sulfate
  2. filtrationfiltered
  3. concentrationconcentrated in vacuo
  4. customto provide a light yellow solid, which
  5. customto precipitate
  6. filtrationthe solid was collected by filtration
  7. washwashed with heptane
  8. washwashed with diethyl ether

출처 및 근거

ORD 기록
ord-0724ee0a385543c1a871cd78eed43e10
출처 데이터셋
uspto-grants-2013_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08518944B2

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