4-Methoxybenzylamine → (3S,6R)-1-[2-amino-6-(4-cyano-3-fluorophenyl)-4-pyrimidinyl]-6-methyl-N-{[4-(methyloxy)phenyl]methyl}-3-piperidinecarboxamide

HRID 2367485노트

반응식

HRID 2367485 반응식
[NH2:1][C:2]1[N:7]=[C:6]([N:8]2[C@H:13]([CH3:14])[CH2:12][CH2:11][C@H:10]([C:15](O)=[O:16])[CH2:9]2)[CH:5]=[C:4]([C:18]2[CH:23]=[CH:22][C:21]([C:24]#[N:25])=[C:20]([F:26])[CH:19]=2)[N:3]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[CH3:60][O:61][C:62]1[CH:67]=[CH:66][C:65]([CH2:68][NH2:69])=[CH:64][CH:63]=1>CN(C=O)C>[NH2:1][C:2]1[N:7]=[C:6]([N:8]2[C@H:13]([CH3:14])[CH2:12][CH2:11][C@H:10]([C:15]([NH:69][CH2:68][C:65]3[CH:66]=[CH:67][C:62]([O:61][CH3:60])=[CH:63][CH:64]=3)=[O:16])[CH2:9]2)[CH:5]=[C:4]([C:18]2[CH:23]=[CH:22][C:21]([C:24]#[N:25])=[C:20]([F:26])[CH:19]=2)[N:3]=1

참가 물질

6

반응물 4

HCID 754524-MethoxybenzylamineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 51356008(3S,6R)-1-[2-Amino-6-(4-cyano-3-fluorophenyl)-4-pyrimidinyl]-6-methyl-3-piperidinecarboxylic acid

생성물 1

HCID 58504502(3S,6R)-1-[2-amino-6-(4-cyano-3-fluorophenyl)-4-pyrimidinyl]-6-methyl-N-{[4-(methyloxy)phenyl]methyl}-3-piperidinecarboxamide수율 89.5%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of (3S,6R)-1-[2-amino-6-(4-cyano-3-fluorophenyl)-4-pyrimidinyl]-6-methyl-3-piperidinecarboxylic acid (170 mg, 0.478 mmol) and HATU (218 mg, 0.574 mmol) in DMF (3 mL) was added Hunig's base (0.167 mL, 0.957 mmol), and the mixture was stirred at room temperature for 5 minutes. Then 1-[4-(methyloxy)phenyl]methanamine (65.6 mg, 0.478 mmol) was added, and the reaction mixture was stirred at room temperature for 0.5 hours. LCMS showed reaction was completed. The reaction was poured onto water, and the formed solid was filtered, washed by water and dried to give the title compound (203 mg) as a yellow solid. LC-MS (ES) m/z=475 [M+H]+.

후처리

  1. stirringthe reaction mixture was stirred at room temperature for 0.5 hours
  2. customreaction
  3. additionThe reaction was poured onto water
  4. filtrationthe formed solid was filtered
  5. washwashed by water
  6. customdried

출처 및 근거

ORD 기록
ord-c280b840e5eb442ba53fc7484ebb4aa9
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08697685B2

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