Diisopropylethylamine → 3,5-dichloro-4-[(2-cyclopentyl-6-methyl-5-oxo-2,6,9,11-tetrazabicyclo[5.4.0]undeca-7,9,11-trien-10-yl)amino]-2-fluoro-N-(1-methyl-4-piperidyl)benzamide

HRID 2234312노트

반응식

HRID 2234312 반응식
[Cl:1][C:2]1[C:3]([F:31])=[C:4]([CH:8]=[C:9]([Cl:30])[C:10]=1[NH:11][C:12]1[N:22]=[C:21]2[C:15]([N:16]([CH3:29])[C:17](=[O:28])[CH2:18][CH2:19][N:20]2[CH:23]2[CH2:27][CH2:26][CH2:25][CH2:24]2)=[CH:14][N:13]=1)[C:5](O)=[O:6].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:56][CH:57]1[CH2:62][CH2:61][N:60]([CH3:63])[CH2:59][CH2:58]1.C(N(C(C)C)CC)(C)C>CN(C=O)C>[Cl:1][C:2]1[C:3]([F:31])=[C:4]([CH:8]=[C:9]([Cl:30])[C:10]=1[NH:11][C:12]1[N:22]=[C:21]2[C:15]([N:16]([CH3:29])[C:17](=[O:28])[CH2:18][CH2:19][N:20]2[CH:23]2[CH2:27][CH2:26][CH2:25][CH2:24]2)=[CH:14][N:13]=1)[C:5]([NH:56][CH:57]1[CH2:62][CH2:61][N:60]([CH3:63])[CH2:59][CH2:58]1)=[O:6]

참가 물질

6

반응물 4

HCID 81531DiisopropylethylamineHCID 27375314-Amino-1-methylpiperidineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 866175623,5-Dichloro-4-[(2-cyclopentyl-6-methyl-5-oxo-2,6,9,11-tetrazabicyclo[5.4.0]undeca-7,9,11-trien-10-yl)amino]-2-fluoro-benzoic acid2회

생성물 1

HCID 866175613,5-dichloro-4-[(2-cyclopentyl-6-methyl-5-oxo-2,6,9,11-tetrazabicyclo[5.4.0]undeca-7,9,11-trien-10-yl)amino]-2-fluoro-N-(1-methyl-4-piperidyl)benzamide수율 66%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

3,5-dichloro-4-[(2-cyclopentyl-6-methyl-5-oxo-2,6,9,11-tetrazabicyclo[5.4.0]undeca-7,9,11-trien-10-yl)amino]-2-fluoro-benzoic acid (Intermediate 221; 85 mg, 0.18 mmol), HATU (104 mg, 0.27 mmol) and 4-amino-1-methylpiperidine (32 mg, 0.27 mmol) were stirred in DMF (3 mL) and diisopropylethylamine (95 μl, 0.54 mmol) added. The mixture was stirred for 2 hours and absorbed on to an SCX column, which was subsequently washed with methanol and eluted with ammonia in methanol. Product containing fractions were combined and evaporated and the residue purified by column chromatography (4% ammonia in methanol/DCM) to yield the title compound as a white solid (67 mg, 66%).

후처리

  1. customabsorbed on to an SCX column, which
  2. washwas subsequently washed with methanol
  3. washeluted with ammonia in methanol
  4. additionProduct containing fractions
  5. customevaporated
  6. customthe residue purified by column chromatography (4% ammonia in methanol/DCM)

출처 및 근거

ORD 기록
ord-27fcd5d0ea5841b9847fde6b9d12cb75
출처 데이터셋
uspto-grants-2010_05
특허 번호
US07709471B2

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