Benzyl Chloride → 5-Methyl-pyridine-2-sulfonic acid [2-(2-aminomethyl-pyridin-4-yl)-6-methoxy-5-(2-methoxy-phenoxy)-pyrimidin-4-yl]-amide hydrochloride

HRID 1066513

반응식

HRID 1066513 반응식
[C:1]([C:3]1[CH:8]=[C:7]([C:9]2[N:14]=[C:13]([NH:15][S:16]([C:19]3[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][N:20]=3)(=[O:18])=[O:17])[C:12]([O:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[O:33][CH3:34])=[C:11]([O:35][CH3:36])[N:10]=2)[CH:6]=[CH:5][N:4]=1)#[N:2].C([Cl:44])C1C=CC=CC=1>CO.[Pd]>[ClH:44].[NH2:2][CH2:1][C:3]1[CH:8]=[C:7]([C:9]2[N:14]=[C:13]([NH:15][S:16]([C:19]3[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][N:20]=3)(=[O:18])=[O:17])[C:12]([O:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[O:33][CH3:34])=[C:11]([O:35][CH3:36])[N:10]=2)[CH:6]=[CH:5][N:4]=1

참가 물질

5

반응물 2

HCID 7503Benzyl ChlorideHCID 99358945-Methyl-pyridine-2-sulfonic acid [2-(2-cyano-pyridin-4-yl)-6-methoxy-5-(2-methoxy-phenoxy)-pyrimidin-4-yl]-amide

생성물 1

HCID 867569945-Methyl-pyridine-2-sulfonic acid [2-(2-aminomethyl-pyridin-4-yl)-6-methoxy-5-(2-methoxy-phenoxy)-pyrimidin-4-yl]-amide hydrochloride

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 887Methanol용매

실험 절차

A solution of 100 mg of 5-methyl-pyridine-2-sulfonic acid [2-(2-cyano-pyridin-4-yl)-6-methoxy-5-(2-methoxy-phenoxy)-pyrimidin-4-yl]-amide, product of example 19, dissolved in MeOH (5 ml), was treated with 47.5 mg of benzyl chloride, 10 mg of palladium on charcoal (10%) and then hydrogenated at RT for hours until TLC analysis indicated completion of transformation. The catalyst was filtered off, and the solution concentrated in vacuo. The crystalline solid that precipitated was collected by filtration, washed with ether and dried in a high vacuum to give 5-methyl-pyridine-2-sulfonic acid [2-(2-aminomethyl-pyridin-4-yl)-6-methoxy-5-(2-methoxy-phenoxy)-pyrimidin-4-yl]-amide hydrochloride as light yellow crystals. ISP mass spectrum, m/e 509.3 (M+1 calculated for C24H24N6O5S: 509).

후처리

  1. waithydrogenated at RT for hours until TLC analysis
  2. filtrationThe catalyst was filtered off
  3. concentrationthe solution concentrated in vacuo
  4. customThe crystalline solid that precipitated
  5. filtrationwas collected by filtration
  6. washwashed with ether
  7. customdried in a high vacuum

출처 및 근거

ORD 기록
ord-587b358c8d2f457da7e3776437dc0fe4
출처 데이터셋
uspto-grants-2001_06
특허 번호
US06242601B1

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