Potassium Cyanide → HCID 67167406、化合物

HRID 874714ノート

反応式

HRID 874714 の反応式
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

参加物

5

反応物 2

HCID 9032Potassium CyanideHCID 67167119HCID 67167119、化合物

生成物 1

HCID 67167406HCID 67167406、化合物収率 83.2%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 962Water溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-3fecae9254044482bb70d87040a82d7a
出典データセット
uspto-grants-2015_03
特許番号
US08980926B2

反応ノート

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