Triphenylphosphine → Methyl 4-[4-amino-2-ethoxymethyl-7-(pyridin-3-yl)-1h-imidazo[4,5-c]quinolin-1-yl]butane-1-sulfonamide

HRID 9425

반응식

HRID 9425 반응식
[CH3:1][CH:2]([S:25]([NH2:28])(=[O:27])=[O:26])[CH2:3][CH2:4][CH2:5][N:6]1[C:18]2[C:17]3[CH:16]=[CH:15][C:14](Br)=[CH:13][C:12]=3[N:11]=[C:10]([NH2:20])[C:9]=2[N:8]=[C:7]1[CH2:21][O:22][CH2:23][CH3:24].B1([C:35]2[CH:40]=[CH:39][CH:38]=[N:37][CH:36]=2)OCCCO1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:1][CH:2]([S:25]([NH2:28])(=[O:27])=[O:26])[CH2:3][CH2:4][CH2:5][N:6]1[C:18]2[C:17]3[CH:16]=[CH:15][C:14]([C:35]4[CH:36]=[N:37][CH:38]=[CH:39][CH:40]=4)=[CH:13][C:12]=3[N:11]=[C:10]([NH2:20])[C:9]=2[N:8]=[C:7]1[CH2:21][O:22][CH2:23][CH3:24]

참가 물질

5

반응물 3

HCID 11776TriphenylphosphineHCID 41980053-(1,3,2-Dioxaborinan-2-yl)pyridine2회HCID 68819757Methyl 4-(4-amino-7-bromo-2-ethoxymethyl-1h-imidazo[4,5-c]quinolin-1-yl)butane-1-sulfonamide

생성물 1

HCID 68818760Methyl 4-[4-amino-2-ethoxymethyl-7-(pyridin-3-yl)-1h-imidazo[4,5-c]quinolin-1-yl]butane-1-sulfonamide수율 97.9%

시약·촉매·용매 1

HCID 167845palladium(II) acetate촉매

실험 절차

Methyl 4-(4-amino-7-bromo-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)butane-1-sulfonamide (0.78 g, 1.7 mmol) and pyridine-3-boronic acid 1,3-propanediol cyclic ester (0.33 g, 2.0 mmol) were coupled according to the method described in Part J of Example 1. The reaction was heated at reflux for 15 hours, at which time additional pyridine-3-boronic acid 1,3-propanediol cyclic ester, palladium acetate, and triphenylphosphine were added, and the reaction was heated for an additional three hours. The work-up procedure used in Part F of Examples 125–135 was followed. The crude product was purified twice by column chromatography on silica gel (eluting with chloroform:CMA in a gradient from 95:5 to 70:30) and then triturated with methanol, isolated by filtration, and dried for eight hours under high vacuum at 100° C. to provide 0.78 g of methyl 4-[4-amino-2-ethoxymethyl-7-(pyridin-3-yl)-1H-imidazo[4,5-c]quinolin-1-yl]butane-1-sulfonamide as off-white needles, mp 216–218° C.

후처리

  1. temperatureThe reaction was heated
  2. additionwere added
  3. temperaturethe reaction was heated for an additional three hours
  4. customThe crude product was purified twice by column chromatography on silica gel (
  5. washeluting with chloroform
  6. customCMA in a gradient from 95:5 to 70:30) and then triturated with methanol
  7. customisolated by filtration
  8. customdried for eight hours under high vacuum at 100° C.

출처 및 근거

ORD 기록
ord-db20c0a683854d36b57eabfee6614a32
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07091214B2

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