Diisopropylethylamine → methyl (R)-3-((2-(3-(2-ethoxyphenoxy)piperidin-1-yl)pyrimidine-5-carboxamido)methyl)-5-methoxybenzoate

HRID 59909

반응식

HRID 59909 반응식
[CH2:1]([O:3][C:4]1[CH:25]=[CH:24][CH:23]=[CH:22][C:5]=1[O:6][C@@H:7]1[CH2:12][CH2:11][CH2:10][N:9]([C:13]2[N:18]=[CH:17][C:16]([C:19](O)=[O:20])=[CH:15][N:14]=2)[CH2:8]1)[CH3:2].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C.Cl.[NH2:60][CH2:61][C:62]1[CH:63]=[C:64]([CH:69]=[C:70]([O:72][CH3:73])[CH:71]=1)[C:65]([O:67][CH3:68])=[O:66]>ClCCl>[CH2:1]([O:3][C:4]1[CH:25]=[CH:24][CH:23]=[CH:22][C:5]=1[O:6][C@@H:7]1[CH2:12][CH2:11][CH2:10][N:9]([C:13]2[N:18]=[CH:17][C:16]([C:19]([NH:60][CH2:61][C:62]3[CH:63]=[C:64]([CH:69]=[C:70]([O:72][CH3:73])[CH:71]=3)[C:65]([O:67][CH3:68])=[O:66])=[O:20])=[CH:15][N:14]=2)[CH2:8]1)[CH3:2]

참가 물질

6

반응물 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 118366221(R)-2-(3-(2-ethoxyphenoxy)piperidin-1-yl)pyrimidine-5-carboxylic acidHCID 118366264Methyl 3-(aminomethyl)-5-methoxybenzoate hydrochloride

생성물 1

HCID 131737072methyl (R)-3-((2-(3-(2-ethoxyphenoxy)piperidin-1-yl)pyrimidine-5-carboxamido)methyl)-5-methoxybenzoate수율 87%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a suspension of (R)-2-(3-(2-ethoxyphenoxy)piperidin-1-yl)pyrimidine-5-carboxylic acid (50 mg, 0.14 mmol) and HATU (63 mg, 0.17 mmol) in dry dichloromethane (3 mL) was added N,N-diisopropylethylamine (0.075 mL, 0.42 mmol) at 20-25° C. The mixture was stirred for 10 min, then methyl 3-(aminomethyl)-5-methoxybenzoate hydrochloride was added (33 mg, 0.14 mmol) at 20-25° C. The reaction mixture was stirred at 20-25° C. for 1 hour. The mixture was concentrated under reduced pressure and the resulting residue was dissolved in ethyl acetate (10 mL), washed with water (2 times with 10 mL), and dried over NaSO4. The organics were concentrated under reduced pressure to obtain methyl (R)-3-((2-(3-(2-ethoxyphenoxy)piperidin-1-yl)pyrimidine-5-carboxamido)methyl)-5-methoxybenzoate (65 mg, 87%).

후처리

  1. stirringThe reaction mixture was stirred at 20-25° C. for 1 hour
  2. concentrationThe mixture was concentrated under reduced pressure
  3. dissolutionthe resulting residue was dissolved in ethyl acetate (10 mL)
  4. washwashed with water (2 times with 10 mL)
  5. dry with materialdried over NaSO4
  6. concentrationThe organics were concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-46abd95da3f147deb299b0b480716d06
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09440949B2

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