Potassium Carbonate → HCID 178511039, 화합물

HRID 64324노트

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HRID 64324 반응식
[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]

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 537695834-Bromobut-2-enenitrileHCID 178513491HCID 178513491, 화합물

생성물 1

HCID 178511039HCID 178511039, 화합물수율 6%

시약·촉매·용매 1

HCID 180Acetone용매2회

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-0cc1b7cd3ebc4b9aae73117bf38dc2f7
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09447106B2

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