Diisopropylethylamine → N-[(3-Bromo-2-fluorophenyl)methyl]-N'-{[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}-1,3-benzenedicarboxamide

HRID 564564노트

반응식

HRID 564564 반응식
[CH2:1]([N:3]1[C:7]2=[N:8][C:9]([CH2:32][CH3:33])=[C:10]([CH2:19][NH:20][C:21]([C:23]3[CH:24]=[C:25]([CH:29]=[CH:30][CH:31]=3)[C:26](O)=[O:27])=[O:22])[C:11]([NH:12][CH:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)=[C:6]2[CH:5]=[N:4]1)[CH3:2].Cl.[Br:35][C:36]1[C:37]([F:44])=[C:38]([CH2:42][NH2:43])[CH:39]=[CH:40][CH:41]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C>C(Cl)Cl>[Br:35][C:36]1[C:37]([F:44])=[C:38]([CH2:42][NH:43][C:26]([C:25]2[CH:29]=[CH:30][CH:31]=[C:23]([C:21]([NH:20][CH2:19][C:10]3[C:11]([NH:12][CH:13]4[CH2:14][CH2:15][O:16][CH2:17][CH2:18]4)=[C:6]4[CH:5]=[N:4][N:3]([CH2:1][CH3:2])[C:7]4=[N:8][C:9]=3[CH2:32][CH3:33])=[O:22])[CH:24]=2)=[O:27])[CH:39]=[CH:40][CH:41]=1

참가 물질

6

반응물 4

HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 46942196(3-broMo-2-fluorophenyl)MethanaMine hydrochlorideHCID 578132773-[({[1,6-Diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}amino)carbonyl]benzoic Acid

생성물 1

HCID 57813438N-[(3-Bromo-2-fluorophenyl)methyl]-N'-{[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}-1,3-benzenedicarboxamide

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A mixture of 3-[({[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}amino)carbonyl]benzoic acid (210 mg, 0.466 mmol), [(3-bromo-2-fluorophenyl)methyl]amine hydrochloride (123 mg, 0.513 mmol), HBTU (194 mg, 0.513 mmol) and diisopropyl ethyl amine (0.5 mL) in DCM (10 mL) was stirred at room temperature for about 5 h. It was concentrated, mixed with EtOAc (25 mL), washed with aqueous NaHCO3 (25 mL) and then NH4Cl (25 mL). The organic layer was collected, dried and concentrated to afford the desired product as a crude mixture (330 mg).

후처리

  1. concentrationIt was concentrated
  2. additionmixed with EtOAc (25 mL)
  3. washwashed with aqueous NaHCO3 (25 mL)
  4. customThe organic layer was collected
  5. customdried
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-e4e4e7e872e24d1e916be6c6477088df
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08067408B2

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