Sodium hydride → HCID 178455298, 화합물

HRID 1852878노트

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HRID 1852878 반응식
[H-].[Na+].[Si:3]([O:10][CH2:11][CH2:12][OH:13])([C:6]([CH3:9])([CH3:8])[CH3:7])([CH3:5])[CH3:4].[Cl:14][C:15]1[N:20]=[C:19]([C:21]2[C:22](F)=[N:23][CH:24]=[C:25]([Cl:27])[CH:26]=2)[C:18]2[N:29]([CH2:41][C@H:42]3[CH2:47][CH2:46][C@H:45]([CH3:48])[CH2:44][CH2:43]3)[C:30]([N:32]3[CH2:37][CH2:36][O:35][C@@H:34]4[CH2:38][CH2:39][CH2:40][C@@H:33]34)=[N:31][C:17]=2[CH:16]=1>CN(C=O)C>[Si:3]([O:10][CH2:11][CH2:12][O:13][C:22]1[C:21]([C:19]2[C:18]3[N:29]([CH2:41][C@H:42]4[CH2:47][CH2:46][C@H:45]([CH3:48])[CH2:44][CH2:43]4)[C:30]([N:32]4[CH2:37][CH2:36][O:35][C@@H:34]5[CH2:38][CH2:39][CH2:40][C@@H:33]45)=[N:31][C:17]=3[CH:16]=[C:15]([Cl:14])[N:20]=2)=[CH:26][C:25]([Cl:27])=[CH:24][N:23]=1)([C:6]([CH3:8])([CH3:9])[CH3:7])([CH3:5])[CH3:4]

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 111376652-(tert-Butyl(dimethyl)silyl)oxyethanolHCID 178461232HCID 178461232, 화합물

생성물 1

HCID 178455298HCID 178455298, 화합물

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
0 °C

실험 절차

NaH (24 mg, 0.6 mmol) was added to solution of 2-((tert-butyldimethylsilyl)oxy)ethanol (70 mg, 0.4 mmol) in DMF (1.0 mL) at 0° C., and the reaction was stirred at 0° C. for 30 minutes. A solution of 6-chloro-4-(5-chloro-2-fluoropyridin-3-yl)-2-[(trans)-hexahydrocyclopenta[b][1,4]oxazin-4(4aH)-yl]-3-[(trans-4-methylcyclohexyl)methyl]-3H-imidazo[4,5-c]pyridine (racemic, Example 18.1, Step 1; 100 mg, 0.2 mmol) was added, and the reaction was stirred at 0° C. for 30 minutes. The reaction was quenched by adding saturated aqueous NH4Cl solution and extracted using EtOAc. The organic layer was washed with brine, dried over Na2SO4, filtered and concentrated. Purification of the residue on a silica gel column with 0 to 50% EtOAc/hexane afforded 4-[2-(2-{[tert-butyl(dimethyl)silyl]oxy}ethoxy)-5-chloropyridin-3-yl]-6-chloro-2-[(trans)-hexahydrocyclopenta[b][1,4]oxazin-4(4aH)-yl]-3-[(trans-4-methylcyclohexyl)methyl]-3H-imidazo[4,5-c]pyridine (racemic). MS APCI calc'd. for C34H49Cl2N5O3Si [M+H]+ 674. found 674.

후처리

  1. stirringthe reaction was stirred at 0° C. for 30 minutes
  2. customThe reaction was quenched
  3. additionby adding saturated aqueous NH4Cl solution
  4. extractionextracted
  5. washThe organic layer was washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customPurification of the residue on a silica gel column with 0 to 50% EtOAc/hexane

출처 및 근거

ORD 기록
ord-98931475e10d4e98b950a71902d841ba
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08962611B2

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