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Dimethylformamide → HCID 66748126, 화합물

HRID 2402159
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HRID 2402159 반응식
[H-].[Na+].CN(C)C=O.[OH:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]=[CH:11][N:10]=1.Br[CH2:20][C:21]1[C:25]([C:26]#[N:27])=[C:24]([N:28]2[CH2:33][CH2:32][O:31][CH2:30][CH2:29]2)[S:23][C:22]=1[C:34]([O:36][CH3:37])=[O:35]>CO.C(Cl)Cl>[C:26]([C:25]1[C:21]([CH2:20][N:10]2[C:9](=[O:8])[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[N:12]=[CH:11]2)=[C:22]([C:34]([O:36][CH3:37])=[O:35])[S:23][C:24]=1[N:28]1[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1)#[N:27]
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참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 66748038HCID 66748038, 화합물HCID 178517962HCID 178517962, 화합물

생성물 1

HCID 66748126HCID 66748126, 화합물수율 87.4%

시약·촉매·용매 1

HCID 21226129Dichloromethane methanol용매

실험 절차

Under N2 atmosphere Sodium hydride (23.0 mg, 0.910 mmol) was suspended in anhydrous N,N-Dimethylformamide (3.0 mL, 39 mmol), cooled with ice bath and stirred for 10 min. 4-hydroxyquinazoline (0.120 g, 0.821 mmol) was added and the clear solution was stirred at r.t. for 10 min, cooled with ice bath. Methyl 3-(bromomethyl)-4-cyano-5-(morpholin-4-yl)thiophene-2-carboxylate (0.203 g, 0.588 mmol) was added and the reddish-brown solution was stirred with cooling for 40 min. The mixture was quenched with saturated NH4Cl aqueous solution, extracted with EtOAc. The EtOAc solution was washed with water (3×) then brine, dried over Na2SO4, filtered, rotavaped to give a crude solid. Chromatograph in a silica gel column using MeOH/DCM (0/100 to 5/95) afforded a solid product (0.211 g, yield 87.4%). LC/MS: (FA) ES+ 411. 1H NMR (400 MHz, d-chloroform) δ 8.30 (m, 1H), 8.26 (s, 1H), 7.68-7.76 (m, 2H), 7.45-7.49 (m, 1H), 5.43 (s, 2H), 3.83-3.85 (m, 4H), 3.82 (s, 3H), 3.59-3.62 (m, 4H).

후처리

  1. temperaturecooled with ice bath
  2. stirringthe clear solution was stirred at r.t. for 10 min
  3. temperaturecooled with ice bath
  4. stirringthe reddish-brown solution was stirred
  5. temperaturewith cooling for 40 min
  6. customThe mixture was quenched with saturated NH4Cl aqueous solution
  7. extractionextracted with EtOAc
  8. washThe EtOAc solution was washed with water (3×)
  9. dry with materialbrine, dried over Na2SO4
  10. filtrationfiltered
  11. customto give a crude solid

출처 및 근거

ORD 기록
ord-eeaeb1c6667d4bec9bd5921794d026e7
출처 데이터셋
uspto-grants-2014_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08796271B2

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