3-Fluoro-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine → N-(4-(Chlorodifluoromethoxy)phenyl)-5'-fluoro-2-((2-hydroxyethyl)(methyl)amino)-[3,3'-bipyridine]-5-carboxamide

HRID 924030

반응식

HRID 924030 반응식
Br[C:2]1[C:3]([N:22]([CH2:24][CH2:25][OH:26])[CH3:23])=[N:4][CH:5]=[C:6]([CH:21]=1)[C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][C:17]([Cl:20])([F:19])[F:18])=[CH:12][CH:11]=1)=[O:8].[F:27][C:28]1[CH:29]=[N:30][CH:31]=[C:32](B2OC(C)(C)C(C)(C)O2)[CH:33]=1>>[Cl:20][C:17]([F:19])([F:18])[O:16][C:13]1[CH:14]=[CH:15][C:10]([NH:9][C:7]([C:6]2[CH:21]=[C:2]([C:32]3[CH:31]=[N:30][CH:29]=[C:28]([F:27])[CH:33]=3)[C:3]([N:22]([CH2:24][CH2:25][OH:26])[CH3:23])=[N:4][CH:5]=2)=[O:8])=[CH:11][CH:12]=1

참가 물질

3

반응물 2

HCID 164142683-Fluoro-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)pyridineHCID 899067025-bromo-N-(4-(chlorodifluoromethoxy)phenyl)-6-((2-hydroxyethyl)(methyl)amino)nicotinamide

생성물 1

HCID 118195361N-(4-(Chlorodifluoromethoxy)phenyl)-5'-fluoro-2-((2-hydroxyethyl)(methyl)amino)-[3,3'-bipyridine]-5-carboxamide

실험 절차

The title compound was prepared in an analogous fashion to that described in Example 169 using 5-bromo-N-(4-(chlorodifluoromethoxy)phenyl)-6-((2-hydroxyethyl)(methyl)amino)nicotinamide (Stage 179.1) and 3-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine to afford an off-white foam. HPLC (Condition 4) tR=5.51 min, UPLC-MS (Condition 3) tR=1.07 min, m/z=467.3 [M+H]+; 1H-NMR (400 MHz, DMSO-d6) δ ppm 2.69 (s, 3H) 3.39-3.61 (m, 4H) 4.65 (t, J=5.08 Hz, 1H) 7.33 (d, J=8.99 Hz, 2H) 7.77-7.94 (m, 3H) 8.11 (d, J=2.35 Hz, 1H) 8.50-8.63 (m, 2H) 8.74 (d, J=2.35 Hz, 1H) 10.21 (s, 1H).

후처리

  1. customto afford an off-white foam

출처 및 근거

ORD 기록
ord-d57e32c301e0467891b3bdfd9fd8bc72
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09278981B2

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