1-(2-Pyrimidinyl)piperazine → HCID 178489387, 화합물

HRID 1171122노트

반응식

HRID 1171122 반응식
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:17]2[C:12](=[N:13][CH:14]=[C:15]([C:18]3[CH:19]=[C:20]([CH:24]=[CH:25][CH:26]=3)[C:21](O)=[O:22])[CH:16]=2)[NH:11][N:10]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[N:51]1[CH:56]=[CH:55][CH:54]=[N:53][C:52]=1[N:57]1[CH2:62][CH2:61][NH:60][CH2:59][CH2:58]1>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:17]2[C:12](=[N:13][CH:14]=[C:15]([C:18]3[CH:19]=[C:20]([C:21]([N:60]4[CH2:61][CH2:62][N:57]([C:52]5[N:51]=[CH:56][CH:55]=[CH:54][N:53]=5)[CH2:58][CH2:59]4)=[O:22])[CH:24]=[CH:25][CH:26]=3)[CH:16]=2)[NH:11][N:10]=1

참가 물질

5

반응물 3

HCID 887471-(2-Pyrimidinyl)piperazineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 178489390HCID 178489390, 화합물

생성물 1

HCID 178489387HCID 178489387, 화합물수율 29.3%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 3-[3-(2-methoxy-phenyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-benzoic acid (18 mg, 0.05 mmol) in DMF (1 mL) was added HATU (20 mg, 0.05 mmol) and 1-(2-pyrimidyl)piperazine (11 uL, 0.08 mmol). The reaction solution was stirred for 16 hours at ambient temperature. The crude product was extracted into ethyl acetate and washed with H2O. The organic layer was dried over Na2SO4, filtered, and adsorbed onto silica gel. Purification by flash chromatography with a gradient of ethyl acetate (containing 10% MeOH) and hexanes afforded the title compound as a white powder (7.2 mg, 28% yield). 1H NMR (500 MHz, CD3OD) δ 8.85 (d, J=2 Hz, 1H), 8.42 (d, J=2 Hz, 1H), 8.35 (d, J=4.5 Hz, 2H), 7.83 (d, J=8 Hz, 1H), 7.79 (s, 1H), 7.64 (m, 2H), 7.50 (m, 2H), 7.20 (d, J=8.5 Hz, 1H), 7.11 (t, J=8 Hz, 1H), 6.64 (t, J=4.5 Hz, 1H), 3.96 (br s, 2H), 3.89 (s, 3H), 3.86 (br s, 4H), 3.60 (br s, 2H). MS: m/z 492.1 (M+H+).

후처리

  1. extractionThe crude product was extracted into ethyl acetate
  2. washwashed with H2O
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. customPurification by flash chromatography with a gradient of ethyl acetate (containing 10% MeOH) and hexanes

출처 및 근거

ORD 기록
ord-9b4cce4e78564b719f78231d2c6797d9
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07829558B2

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