Dimethylformamide → HCID 57731458, 화합물

HRID 2234707노트

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HRID 2234707 반응식
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:17]2[C:12](=[N:13][CH:14]=[C:15]([C:18]3[N:23]=[C:22]([CH2:24][C:25]([N:27]([CH3:29])[CH3:28])=[O:26])[CH:21]=[N:20][CH:19]=3)[CH:16]=2)[N:11](S(C2C=CC(C)=CC=2)(=O)=O)[CH:10]=1.CN(C)C=O.[OH-].[K+]>CO>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:17]2[C:12](=[N:13][CH:14]=[C:15]([C:18]3[N:23]=[C:22]([CH2:24][C:25]([N:27]([CH3:29])[CH3:28])=[O:26])[CH:21]=[N:20][CH:19]=3)[CH:16]=2)[NH:11][CH:10]=1

참가 물질

5

반응물 3

HCID 6228DimethylformamideHCID 14797Potassium HydroxideHCID 59297027HCID 59297027, 화합물

생성물 1

HCID 57731458HCID 57731458, 화합물수율 14.1%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

2-{6-[3-(2-Methoxy-phenyl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-pyrazin-2-yl}-N,N-dimethyl-acetamide (56.6 mg, 0.104 mmol) was dissolved in methanol (0.5 mL) and dimethylformamide (0.5 mL) and 50% w/v aqueous potassium hydroxide (0.2 mL) was added. After 5 hours, the reaction was quenched by addition of acetic acid (0.2 mL). The mixture was carefully poured into saturated sodium bicarbonate and extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered and dried to a residue which was purified by preparative HPLC to afford 2-{6-[3-(2-methoxy-phenyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-pyrazin-2-yl}-N,N-dimethyl-acetamide (5.7 mg, 14.1%). 1H-NMR (500 MHz, dimethylsulfoxide-d6) δ 2.74 (s, 3H), 2.90 (s, 3H), 3.78 (s, 3H), 3.96 (s, 2H), 7.01 (dt, J=1, J=7.5 Hz, 1H), 7.11 (br d, J=8 Hz, 1H), 7.28 (dt, J=1.5, J=8.5 Hz, 1H), 7.50 (dd, J=1.5 Hz, J=7.5 Hz, 1H), 7.77 (d, J=2.0 Hz, 1H), 8.21 (d, J=2.5 Hz, 1H), 8.46 (d, J=2.0 Hz, 1H), 8.56 (d, J=2.5 Hz, 1H), 8.62 (d, J=2.5 Hz, 1H). MS: m/z 388 (M+H+).

후처리

  1. additionwas added
  2. customthe reaction was quenched by addition of acetic acid (0.2 mL)
  3. additionThe mixture was carefully poured into saturated sodium bicarbonate
  4. extractionextracted with ethyl acetate
  5. dry with materialThe combined organic layers were dried over sodium sulfate
  6. filtrationfiltered
  7. customdried to a residue which
  8. customwas purified by preparative HPLC

출처 및 근거

ORD 기록
ord-095f33c2be7e44c2825f02b24bc19151
출처 데이터셋
uspto-grants-2010_05
특허 번호
US07709645B2

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