3-(1,3,2-Dioxaborinan-2-yl)pyridine → HCID 58681256, 화합물

HRID 9486

반응식

HRID 9486 반응식
Br[C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[N:15]([CH2:16][C@H:17]4[CH2:21][O:20][C:19]([CH3:23])([CH3:22])[O:18]4)[C:14]([CH2:24][O:25][CH2:26][CH3:27])=[N:13][C:7]=3[C:8]([NH2:12])=[N:9][C:10]=2[CH:11]=1.B1([C:34]2[CH:39]=[CH:38][CH:37]=[N:36][CH:35]=2)OCCCO1>>[CH3:22][C:19]1([CH3:23])[O:18][C@@H:17]([CH2:16][N:15]2[C:6]3[C:5]4[CH:4]=[CH:3][C:2]([C:34]5[CH:35]=[N:36][CH:37]=[CH:38][CH:39]=5)=[CH:11][C:10]=4[N:9]=[C:8]([NH2:12])[C:7]=3[N:13]=[C:14]2[CH2:24][O:25][CH2:26][CH3:27])[CH2:21][O:20]1

참가 물질

3

반응물 2

HCID 41980053-(1,3,2-Dioxaborinan-2-yl)pyridineHCID 68817937HCID 68817937, 화합물

생성물 1

HCID 58681256HCID 58681256, 화합물수율 54.2%

실험 절차

(S)-7-Bromo-1-[(2,2-dimethyl-1,3-dioxolan-4-yl)methyl]-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-4-amine (2.65 g, 6.09 mmol) and pyridine-3-boronic acid 1,3-propanediol cyclic ester (1.19 g, 7.30 mmol) were coupled according to the method described in Examples 118–121. The work-up procedure described in Part F of Examples 125–135 was followed. The crude product was purified by HPFC (eluting with chloroform:CMA in a gradient from 100:0 to 80:20) followed by recrystallization from acetonitriled to provide 1.43 g of (S)-1-[(2,2-dimethyl-1,3-dioxolan-4-yl)methyl]-2-ethoxymethyl-7-(pyridin-3-yl)-1H-imidazo[4,5-c]quinolin-4-amine as a white solid, mp 157–158° C.

후처리

  1. customThe crude product was purified by HPFC (
  2. washeluting with chloroform
  3. customCMA in a gradient from 100:0 to 80:20) followed by recrystallization

출처 및 근거

ORD 기록
ord-24769b0edb5146748dcf7bf5bec69837
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07091214B2

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