Water → N-(2-(6-(3-(2,6-dichloro-3,5-dimethoxyphenyl)-1-methylureido)pyrimidin-4-ylamino)phenyl)propiolamide

HRID 58151

反応式

HRID 58151 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]1[N:14]=[CH:13][N:12]=[C:11]([N:15]([CH3:31])[C:16]([NH:18][C:19]2[C:24]([Cl:25])=[C:23]([O:26][CH3:27])[CH:22]=[C:21]([O:28][CH3:29])[C:20]=2[Cl:30])=[O:17])[CH:10]=1.C1CCC(N=C=NC2CCCCC2)CC1.[C:47](O)(=[O:50])[C:48]#[CH:49].O>C(Cl)(Cl)Cl>[Cl:25][C:24]1[C:23]([O:26][CH3:27])=[CH:22][C:21]([O:28][CH3:29])=[C:20]([Cl:30])[C:19]=1[NH:18][C:16](=[O:17])[N:15]([C:11]1[N:12]=[CH:13][N:14]=[C:9]([NH:8][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[NH:1][C:47](=[O:50])[C:48]#[CH:49])[CH:10]=1)[CH3:31]

参加物

6

反応物 4

HCID 962WaterHCID 10110Propiolic AcidHCID 10868DicyclohexylcarbodiimideHCID 1180245491-(6-((2-Aminophenyl)amino)pyrimidin-4-yl)-3-(2,6-dichloro-3,5-dimethoxyphenyl)-1-methylurea

生成物 1

HCID 118029221N-(2-(6-(3-(2,6-dichloro-3,5-dimethoxyphenyl)-1-methylureido)pyrimidin-4-ylamino)phenyl)propiolamide収率 9.1%

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒2 回

実験手順

The compound was synthesized following the approach outlined in Procedure 2C (Example 108) modifying step (g) to the following procedure: To a solution of 1-[6-(2-amino-phenylamino)-pyrimidin-4-yl]-3-(2,6-dichloro-3,5-dimethoxy-phenyl)-1-methyl-urea (50 g, 0.108 mmol) and DCC (46 g, 0.22 mmol) in chloroform (50 mL) was added a solution of propiolic acid (16 mg, 0.22 mmol) in chloroform (50 mL) at 0° C., and the resulting mixture was stirred at room temperature overnight. Water (1 mL) was added to quench the reaction. The mixture was concentrated and the residue was purified by reverse phase column and prep-TLC to obtain the title compound (5 mg, yield: 9.1%). 1H NMR (400 MHz, DMSO-d6) δ 12.04 (s, 1H), 10.36 (s, 1H), 9.03 (s, 1H), 8.45 (s, 1H), 7.67 (d, 1H), 7.59 (d, 1H), 7.30-7.25 (m, 2H), 6.96 (s, 1H), 6.50 (s, 1H), 4.42 (s, 1H), 4.00 (s, 6H), 3.35 (s, 3H); MS (ESI): 515 [M+H]+

後処理

  1. customThe compound was synthesized
  2. customto quench
  3. customthe reaction
  4. concentrationThe mixture was concentrated
  5. customthe residue was purified by reverse phase column

出典と根拠

ORDレコード
ord-fa4ad05f7d03422f9cff539c0e5970da
出典データセット
uspto-grants-2016_09
特許番号
US09434697B2

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