Potassium Carbonate → HCID 178511039、化合物

HRID 64324ノート

反応式

HRID 64324 の反応式
[O:1]([C:8]1[CH:13]=[CH:12][C:11]([C:14]2[C:25]([C:26]([NH2:28])=[O:27])=[C:17]3[NH:18][C:19]4[CH2:24][CH2:23][NH:22][CH2:21][C:20]=4[N:16]3[N:15]=2)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:36][CH:37]=[CH:38][C:39]#[N:40]>CC(C)=O>[C:39](/[CH:38]=[CH:37]/[CH2:36][N:22]1[CH2:23][CH2:24][C:19]2[NH:18][C:17]3[N:16]([N:15]=[C:14]([C:11]4[CH:10]=[CH:9][C:8]([O:1][C:2]5[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=5)=[CH:13][CH:12]=4)[C:25]=3[C:26]([NH2:28])=[O:27])[C:20]=2[CH2:21]1)#[N:40]

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 537695834-Bromobut-2-enenitrileHCID 178513491HCID 178513491、化合物

生成物 1

HCID 178511039HCID 178511039、化合物収率 6%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒2 回

実験手順

To a solution of 2-(4-phenoxyphenyl)-5,6,7,8-tetrahydro-4H-pyrazolo[5′,1′:2,3]imidazo[4,5-c]pyridine-3-carboxamide (100 mg, 0.268 mmol) in 10 mL of acetone at RT was added K2CO3 (140 mg, 1.07 mmol). After stirring at RT for 2 hr, 4-bromobut-2-enenitrile (40 mg, 0.268 mmol) in 2 mL of acetone was added and stirred at RT overnight. The mixture was then partitioned between EA (50 mL) and water (100 mL). The aqueous phase was further extracted with 50 mL of EA. The combined organic layers were washed with brine, dried over Na2SO4, concentrated to get crude product which was further purified by pre-TLC (DCM/MeOH=15/1) to afford 7 mg (6%) of (E)-7-(3-cyanoallyl)-2-(4-phenoxyphenyl)-5,6,7,8-tetrahydro-4H-pyrazolo[5′,1′:2,3]imidazo[4,5-c]pyridine-3-carboxamide as a light yellow solid. 1H NMR (400 MHz, CDCl3) δ 10.45 (s, 1H), 7.59 (d, J=8.4 Hz, 2H), 7.42-7.30 (m, 2H), 7.16 (t, J=7.6 Hz, 1H), 7.10 (d, J=8.4 Hz, 2H), 7.06 (d, J=7.6 Hz, 2H), 6.76 (dt, J=16.3, 4.6 Hz, 1H), 5.67 (d, J=16.3 Hz, 1H), 5.62 (s, 2H), 3.82 (s, 2H), 3.41 (d, J=4.6 Hz, 2H), 2.95-2.75 (m, 4H). MS (ESI) m/e [M+1]+ 439.9.

後処理

  1. stirringstirred at RT overnight
  2. customThe mixture was then partitioned between EA (50 mL) and water (100 mL)
  3. extractionThe aqueous phase was further extracted with 50 mL of EA
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customto get crude product which
  8. customwas further purified by pre-TLC (DCM/MeOH=15/1)

出典と根拠

ORDレコード
ord-0cc1b7cd3ebc4b9aae73117bf38dc2f7
出典データセット
uspto-grants-2016_09
特許番号
US09447106B2

反応ノート

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