1,2-Dichloroethane → 3-(1-methyl-1H-imidazol-4-yl)-9-phenyl-8-(4-{[4-(5-pyrimidin-2-yl-4H-1,2,4-triazol-3-yl)piperidin-1-yl]methyl}phenyl)[1,2,4]triazolo[3,4-f]-1,6-naphthyridine

HRID 1678773노트

반응식

HRID 1678773 반응식
[NH:1]([C:3]1[N:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[C:6]([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[C:7]([C:13]1[CH:18]=[CH:17][C:16]([CH2:19][N:20]3[CH2:25][CH2:24][CH:23]([C:26]4[NH:30][C:29]([C:31]5[N:36]=[CH:35][CH:34]=[CH:33][N:32]=5)=[N:28][N:27]=4)[CH2:22][CH2:21]3)=[CH:15][CH:14]=1)=[N:8]2)[NH2:2].C1C=CC2N(O)N=NC=2C=1.[CH3:53][N:54]1[CH:58]=[C:57]([C:59](O)=O)[N:56]=[CH:55]1.CCN(C(C)C)C(C)C.C(Cl)CCl>CN(C=O)C.C(O)(=O)C>[CH3:53][N:54]1[CH:58]=[C:57]([C:59]2[N:12]3[C:3]([C:4]4[CH:5]=[C:6]([C:37]5[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=5)[C:7]([C:13]5[CH:18]=[CH:17][C:16]([CH2:19][N:20]6[CH2:21][CH2:22][CH:23]([C:26]7[NH:30][C:29]([C:31]8[N:36]=[CH:35][CH:34]=[CH:33][N:32]=8)=[N:28][N:27]=7)[CH2:24][CH2:25]6)=[CH:15][CH:14]=5)=[N:8][C:9]=4[CH:10]=[CH:11]3)=[N:1][N:2]=2)[N:56]=[CH:55]1

참가 물질

8

반응물 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 5415091-methyl-1H-imidazole-4-carboxylic acidHCID 178514342HCID 178514342, 화합물

생성물 1

HCID 1784812663-(1-methyl-1H-imidazol-4-yl)-9-phenyl-8-(4-{[4-(5-pyrimidin-2-yl-4H-1,2,4-triazol-3-yl)piperidin-1-yl]methyl}phenyl)[1,2,4]triazolo[3,4-f]-1,6-naphthyridine

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 6228Dimethylformamide용매

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온도
80 °C

실험 절차

To a stirred solution of 11-3 (0.23 g, 0.4 mMol), HOBT (0.06 g, 0.45 mMol), and 1-methyl-1H-imidazole-4-carboxylic acid (0.06 g, 0.45 mMol) in anhydrous DMF (2 mL) was added DIEA (0.13 mL, 0.8 mMol) followed by EDC (0.09 g, 0.5 mMol). The solution was heated in the microwave reactor for 15 minutes at 80° C. Solution was then treated with 0.2 mL of acetic acid and was heated to 80° C. in the microwave reactor for 20 minutes. Upon cooling to room temperature, the solution was passed through a syringe filter and purified on a C18 reverse phase HPLC to give 12-1 as a solid. Mass (M+1) calculated: 632.2742 observed: 632.274

후처리

  1. temperaturewas heated to 80° C. in the microwave reactor for 20 minutes
  2. temperatureUpon cooling to room temperature
  3. customthe solution was passed through a syringe
  4. filtrationfilter
  5. custompurified on a C18 reverse phase HPLC

출처 및 근거

ORD 기록
ord-bf05e73271d44b21928093b65535d432
출처 데이터셋
uspto-grants-2011_08
특허 번호
US08008317B2

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