Diisopropylethylamine → N-(3-amino-2-chloropyridin-4-yl)-2-phenoxyquinoline-8-carboxamide

HRID 1055992

반응식

HRID 1055992 반응식
[O:1]([C:8]1[CH:17]=[CH:16][C:15]2[C:10](=[C:11]([C:18]([OH:20])=[O:19])[CH:12]=[CH:13][CH:14]=2)[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:21][C:22]1[C:27]([NH2:28])=[C:26]([NH2:29])[CH:25]=[CH:24][N:23]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C.CCOC(C)=O>[NH2:28][C:27]1[C:22]([Cl:21])=[N:23][CH:24]=[CH:25][C:26]=1[NH:29][C:18]([C:11]1[CH:12]=[CH:13][CH:14]=[C:15]2[C:10]=1[N:9]=[C:8]([O:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH:17]=[CH:16]2)=[O:20].[NH2:29][C:26]1[CH:25]=[CH:24][N:23]=[C:22]([Cl:21])[C:27]=1[NH:28][C:18]([C:11]1[CH:12]=[CH:13][CH:14]=[C:15]2[C:10]=1[N:9]=[C:8]([O:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH:17]=[CH:16]2)=[O:19]

참가 물질

8

반응물 4

HCID 81531DiisopropylethylamineHCID 2857362-Chloropyridine-3,4-diamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 897820882-Phenoxyquinoline-8-carboxylic acid

생성물 2

HCID 89782020N-(3-amino-2-chloropyridin-4-yl)-2-phenoxyquinoline-8-carboxamideHCID 89782144N-(4-amino-2-chloropyridin-3-yl)-2-phenoxyquinoline-8-carboxamide

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

A mixture of 2-phenoxyquinoline-8-carboxylic acid (119 mg, 0.449 mmol), 2-chloropyridine-3,4-diamine (97 mg, 0.673 mmol, Waterstone Technology, Carmel, Ind.), HATU (341 mg, 0.897 mmol), and DIPEA (235 μl, 1.346 mmol) in DMF (449 μl) was stirred at RT for 2 h. The mixture was diluted with EtOAc (100 ml), added to a separatory funnel, and washed with saturated aq. NaHCO3 (3×75 ml) before the organic layer was separated, dried over Na2SO4, and concentrated. Purification by silica chromatography (100% DCM to 5% MeOH/DCM) provided N-(3-amino-2-chloropyridin-4-yl)-2-phenoxyquinoline-8-carboxamide (or N-(4-amino-2-chloropyridin-3-yl)-2-phenoxyquinoline-8-carboxamide; regioisomer not determined; 178d, 49% yield). MS (ESI, pos. ion) m/z: 391.2 (M+1).

후처리

  1. additionadded to a separatory funnel
  2. washwashed with saturated aq. NaHCO3 (3×75 ml) before the organic layer
  3. customwas separated
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customPurification by silica chromatography (100% DCM to 5% MeOH/DCM)

출처 및 근거

ORD 기록
ord-8ac49400164d4853ab290c11952e5d11
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09394297B2

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