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Sodium Hydroxide → HCID 58917331, 화합물

HRID 547318
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HRID 547318 반응식
[CH2:1]([O:3][CH2:4][C:5]1[N:6]([CH2:19][C:20]2([O:24][CH2:25][CH2:26][S:27]([CH3:30])(=[O:29])=[O:28])[CH2:23][CH2:22][CH2:21]2)[C:7]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[C:9]([NH2:17])[C:8]=2[N:18]=1)[CH3:2].[H][H].[OH-].[Na+]>FC(F)(F)C(O)=O.O.[Pt](=O)=O>[CH2:1]([O:3][CH2:4][C:5]1[N:6]([CH2:19][C:20]2([O:24][CH2:25][CH2:26][S:27]([CH3:30])(=[O:29])=[O:28])[CH2:21][CH2:22][CH2:23]2)[C:7]2[C:16]3[CH2:15][CH2:14][CH2:13][CH2:12][C:11]=3[N:10]=[C:9]([NH2:17])[C:8]=2[N:18]=1)[CH3:2]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 3

HCID 14798Sodium HydroxideHCID 58917341HCID 58917341, 화합물HCID 178418361HCID 178418361, 화합물

생성물 1

HCID 58917331HCID 58917331, 화합물수율 69.1%

시약·촉매·용매 3

HCID 345198Adams' catalyst촉매HCID 962Water용매
HCID 6422
Trifluoroacetic acid
용매

실험 절차

A mixture of 2-(ethoxymethyl)-1-({1-[2-(methylsulfonyl)ethoxy]cyclobutyl}methyl)-1H-imidazo[4,5-c]quinolin-4-amine (prepared as described in Example 26, 0.500 g, 1.16 mmol) and platinum(IV) oxide (0.5 g) in trifluoroacetic acid (5 mL) was hydrogenated on a Parr apparatus at 50 psi (3.5×105 Pa) hydrogen pressure for 1 day. The mixture was filtered through CELITE filter agent, which was washed afterwards with dichloromethane. The filtrate was concentrated under reduced pressure to afford an oil that was suspended in water (20 mL) and adjusted to pH 13 with 50% aqueous sodium hydroxide. A white solid formed that was isolated by filtration, washed with water, and recrystallized from acetonitrile. The crystals were isolated and dried under vacuum at 65° C. to afford 0.35 g of 2-(ethoxymethyl)-1-({1-[2-(methylsulfonyl)ethoxy]cyclobutyl}methyl)-6,7,8,9-tetrahydro-1H-imidazo[4,5-c]quinolin-4-amine as a white powder, mp 186-188° C.

후처리

  1. filtrationThe mixture was filtered through CELITE
  2. filtrationfilter agent, which
  3. washwas washed afterwards with dichloromethane
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customto afford an oil that
  6. customA white solid formed that
  7. customwas isolated by filtration
  8. washwashed with water
  9. customrecrystallized from acetonitrile
  10. customThe crystals were isolated
  11. customdried under vacuum at 65° C.

출처 및 근거

ORD 기록
ord-5629d04b98164af58253436d82c8f3c5
출처 데이터셋
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07939526B2

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