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Benzylamine → (3S,6R)-1-[6-(4-Acetyl-3-fluorophenyl)-2-amino-4-pyrimidinyl]-6-methyl-N-(phenylmethyl)-3-piperidinecarboxamide

HRID 2367479
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HRID 2367479 반응식
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:15]=[C:14]([NH2:16])[N:13]=[C:12]([N:17]3[C@H:22]([CH3:23])[CH2:21][CH2:20][C@H:19]([C:24]([OH:26])=O)[CH2:18]3)[CH:11]=2)=[CH:6][C:5]=1[F:27])(=[O:3])[CH3:2].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.[CH2:61]([NH2:68])[C:62]1[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=1>CN(C=O)C.CCOC(C)=O>[C:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:15]=[C:14]([NH2:16])[N:13]=[C:12]([N:17]3[C@H:22]([CH3:23])[CH2:21][CH2:20][C@H:19]([C:24]([NH:68][CH2:61][C:62]4[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=4)=[O:26])[CH2:18]3)[CH:11]=2)=[CH:6][C:5]=1[F:27])(=[O:3])[CH3:2]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 7504BenzylamineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58504564(3S,6R)-1-[6-(4-Acetyl-3-fluorophenyl)-2-amino-4-pyrimidinyl]-6-methyl-3-piperidinecarboxylic acid

생성물 1

HCID 58504436
(3S,6R)-1-[6-(4-Acetyl-3-fluorophenyl)-2-amino-4-pyrimidinyl]-6-methyl-N-(phenylmethyl)-3-piperidinecarboxamide
수율 88.8%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of (3S,6R)-1-[6-(4-acetyl-3-fluorophenyl)-2-amino-4-pyrimidinyl]-6-methyl-3-piperidinecarboxylic acid (308 mg, 0.827 mmol) and HATU (377 mg, 0.992 mmol) in DMF (3 mL) was added Hunig's base (0.289 ml, 1.654 mmol), and the mixture was stirred at room temperature for 15 minutes. Then benzylamine (0.11 mL, 0.99 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 EtOAc was added to extract the product. The product stayed in the EtOAc layer. The organic solution was concentrated to dryness to give the title compound (339 mg) as a yellow solid. LC-MS (ES) m/z=462 [M+H]+.

후처리

  1. stirringthe reaction mixture was stirred at room temperature for 0.5 hours
  2. customreaction
  3. additionwas added
  4. extractionto extract the product
  5. concentrationThe organic solution was concentrated to dryness

출처 및 근거

ORD 기록
ord-151756cb00634b05a21c17fa0b28f6e0
출처 데이터셋
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08697685B2

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