Diisopropylethylamine → 1-[1-(4-Chloro-3-methyl-benzyl)-piperidin-4-yl]-5-oxo-pyrrolidine-2-carboxylic acid [3-bromo-5-(1-methyl-1H-tetrazol-5-yl)-phenyl]-amide

HRID 241679노트

반응식

HRID 241679 반응식
[Cl:1][C:2]1[CH:23]=[CH:22][C:5]([CH2:6][N:7]2[CH2:12][CH2:11][CH:10]([N:13]3[C:17](=[O:18])[CH2:16][CH2:15][CH:14]3[C:19]([OH:21])=O)[CH2:9][CH2:8]2)=[CH:4][C:3]=1[CH3:24].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[Br:58][C:59]1[CH:60]=[C:61]([NH2:71])[CH:62]=[C:63]([C:65]2[N:69]([CH3:70])[N:68]=[N:67][N:66]=2)[CH:64]=1>CN(C=O)C>[Br:58][C:59]1[CH:60]=[C:61]([NH:71][C:19]([CH:14]2[CH2:15][CH2:16][C:17](=[O:18])[N:13]2[CH:10]2[CH2:11][CH2:12][N:7]([CH2:6][C:5]3[CH:22]=[CH:23][C:2]([Cl:1])=[C:3]([CH3:24])[CH:4]=3)[CH2:8][CH2:9]2)=[O:21])[CH:62]=[C:63]([C:65]2[N:69]([CH3:70])[N:68]=[N:67][N:66]=2)[CH:64]=1

참가 물질

6

반응물 4

HCID 81531Diisopropylethylamine2회HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 667333043-Bromo-5-(1-methyl-1H-tetrazol-5-yl)-phenylamineHCID 667333601-[1-(4-Chloro-3-methyl-benzyl)-piperidin-4-yl]-5-oxo-pyrrolidine-2-carboxylic acid

생성물 1

HCID 667350421-[1-(4-Chloro-3-methyl-benzyl)-piperidin-4-yl]-5-oxo-pyrrolidine-2-carboxylic acid [3-bromo-5-(1-methyl-1H-tetrazol-5-yl)-phenyl]-amide

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 1-[1-(4-Chloro-3-methyl-benzyl)-piperidin-4-yl]-5-oxo-pyrrolidine-2-carboxylic acid as DIPEA salt (2.6 g) in DMF (100 ml) was added DIPEA (2.1 g), and HATU (4 g). 3-Bromo-5-(1-methyl-1H-tetrazol-5-yl)-phenylamine (1.4 g) was added and the reaction stirred overnight at rt. The reaction mixture was filtered and the filtrate partitioned between water and EtOAc. The organic layer was separated, dried and concentrated in vacuum and the residue purified by flash chromatography (DCM:MeOH 100:0 to 95:5 gradient) to give the title compound (400 mg). Rf=0.19 (95:5 DCM:MeOH).

후처리

  1. filtrationThe reaction mixture was filtered
  2. customthe filtrate partitioned between water and EtOAc
  3. customThe organic layer was separated
  4. customdried
  5. concentrationconcentrated in vacuum
  6. customthe residue purified by flash chromatography (DCM:MeOH 100:0 to 95:5 gradient)

출처 및 근거

ORD 기록
ord-5e057ad5c6e04fa9bde98b697937014f
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08653075B2

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