4-Methylmorpholine → N-[1-(2-dimethylamino-ethyl)-1H-indazol-5-yl]-2-(4-phenoxy-phenyl)-acetamide

HRID 1790116노트

반응식

HRID 1790116 반응식
[CH3:1][N:2]([CH3:15])[CH2:3][CH2:4][N:5]1[C:13]2[C:8](=[CH:9][C:10]([NH2:14])=[CH:11][CH:12]=2)[CH:7]=[N:6]1.[O:16]([C:23]1[CH:28]=[CH:27][C:26]([CH2:29][C:30](O)=[O:31])=[CH:25][CH:24]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.Cl.C(N=C=NC(C)(C)CC)C.ON1C2C=CC=CC=2N=N1.CN1CCOCC1>CN(C=O)C>[CH3:1][N:2]([CH3:15])[CH2:3][CH2:4][N:5]1[C:13]2[C:8](=[CH:9][C:10]([NH:14][C:30](=[O:31])[CH2:29][C:26]3[CH:27]=[CH:28][C:23]([O:16][C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=4)=[CH:24][CH:25]=3)=[CH:11][CH:12]=2)[CH:7]=[N:6]1

참가 물질

7

반응물 5

HCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 2390774-Phenoxyphenylacetic acidHCID 22992078Ethyldimethylpropylcarbodiimide hydrochlorideHCID 696529021-(2-dimethylamino-ethyl)-1H-indazol-5-ylamine

생성물 1

HCID 11223730N-[1-(2-dimethylamino-ethyl)-1H-indazol-5-yl]-2-(4-phenoxy-phenyl)-acetamide

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A mixture of 1-(2-dimethylamino-ethyl)-1H-indazol-5-ylamine (42 mg, 0.20 mmol), 4-phenoxy-phenylacetic acid (47 mg, 0.21 mmol), ethyldimethylpropylcarbodiimide hydrochloride (43 mg g, 0.22 mmol), N-hydroxybenzotriazole (30 mg, 0.22 mmol), N-methyl morpholine (46 mg, 0.44 mmol) in 2 mL of DMF was shaken for 6 hours. The mixture was concentrated under reduced pressure, the residue taken up in 1.5 mL of a 1:1 mixture of DMSO/MeOH and purified by preparative reverse-phase HPLC. 1H NMR (300 MHz, DMSO-d6) ppm 2.84 (s, 6H), 3.65 (s, 2H), 3.62 (t, J=6.24, 2H), 4.76 (t, J=6.24, 2H), 6.97–7.00 (m, 4H), 7.11–7.14 (m, 1H), 7.36–7.40 (m, 4H), 7.64 (m, 1H), 7.69 (m, 1H), 8.12 (m, 1H), 8.15 (m, 1H), 9.58 (s, 1H); MS (DCI/NH3) m/z 415 [M+H]+.

후처리

  1. concentrationThe mixture was concentrated under reduced pressure
  2. additionthe residue taken up in 1.5 mL of a 1:1 mixture of DMSO/MeOH
  3. custompurified by preparative reverse-phase HPLC

출처 및 근거

ORD 기록
ord-7eb8b8c43000454c814853505123ccb8
출처 데이터셋
uspto-grants-2006_07
특허 번호
US07071182B2

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