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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
ノート
印刷プレビュー

反応式

HRID 1896664 の反応式
[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
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 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、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒
HCID 6344Dichloromethane溶媒2 回

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-0724ee0a385543c1a871cd78eed43e10
出典データセット
uspto-grants-2013_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08518944B2

反応ノート

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