Potassium Cyanide → HCID 67167406, 화합물

HRID 874714노트

반응식

HRID 874714 반응식
ClC(Cl)[C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]#[C:13][Si:14]([CH3:17])([CH3:16])[CH3:15])=[CH:8][C:7]=1[C:18]([C:20]1[CH:25]=[CH:24][C:23]([C:26]2([C:29]([F:32])([F:31])[F:30])[N:28]=[N:27]2)=[CH:22][CH:21]=1)=[O:19])=O.[C-]#[N:35].[K+]>CCO.O>[NH2:35][C:3]1[C:18]([C:20]2[CH:21]=[CH:22][C:23]([C:26]3([C:29]([F:32])([F:31])[F:30])[N:28]=[N:27]3)=[CH:24][CH:25]=2)([OH:19])[C:7]2[C:6](=[CH:11][CH:10]=[C:9]([C:12]#[C:13][Si:14]([CH3:15])([CH3:16])[CH3:17])[CH:8]=2)[N:5]=1

참가 물질

5

반응물 2

HCID 9032Potassium CyanideHCID 67167119HCID 67167119, 화합물

생성물 1

HCID 67167406HCID 67167406, 화합물수율 83.2%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 962Water용매

실험 절차

2,2-dichloro-N-[2-({4-[3-(trifluoromethyl)diazirin-3-yl]phenyl}carbonyl)-4-[2-(trimethylsilyl)ethynyl]phenyl]acetamide (57 mg, 0.11 mmol, 1 eq.) was dissolved in EtOH (3 mL). Potassium cyanide (9.4 mg, 0.14 mmol, 1.3 eq.) in water (1 mL) was added to the reaction, and the reaction was stirred at room temperature for 16 hours. The EtOH was evaporated, and additional water (8 mL) was added. The reaction was then extracted three times with 5% isopropanol in DCM (20 mL each), and the organic layer was dried over sodium sulfate. The solvent was evaporated, and the residue was purified on silica column (DCM/MeOH, 39:1→19:1→9:1→4:1) to result in 39.2 mg (82%) of the title compound as a yellow solid. 1H NMR (500 MHz, CD3OD) δ 7.44 (d, J=8.5, 2H, Ar—H), 7.29 (dd, J=1.8, 8.8, 1H, Ar—H), 7.22 (d, J=8.3, 2H, Ar—H), 7.02-6.94 (m, 2H, Ar—H), 0.18 (s, 9H, SiC3H9). 13C NMR (126 MHz, CD3OD) δ 180.56 (C—NH2), 156.85 (C—Ar), 144.59 (C—Ar), 140.89 (C—Ar), 135.13 (C—Ar), 129.58 (C—Ar), 127.89 (d, J=0.88, C—Ar), 127.66 (C—Ar), 126.99 (C—Ar), 123.70 (q, J=273.80, CF3), 117.82 (C—Ar), 116.69 (C—Ar), 107.08 (CSi(CH3)3), 92.94 (CCSi(CH3)3), 84.20 (Ar—COH), 29.55 (q, J=40.25, CN2), 0.23 (Si(CH3)3). Exact Mass, 428.13.

후처리

  1. customThe EtOH was evaporated
  2. additionadditional water (8 mL) was added
  3. extractionThe reaction was then extracted three times with 5% isopropanol in DCM (20 mL each)
  4. dry with materialthe organic layer was dried over sodium sulfate
  5. customThe solvent was evaporated
  6. customthe residue was purified on silica column (DCM/MeOH, 39:1→19:1→9:1→4:1)

출처 및 근거

ORD 기록
ord-3fecae9254044482bb70d87040a82d7a
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08980926B2

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