Dimethylformamide → HCID 57731451, 화합물

HRID 2234706노트

반응식

HRID 2234706 반응식
[CH3:1][N:2]([CH3:39])[C:3]([C:5]1[CH:10]=[C:9]([C:11]2[CH:12]=[C:13]3[C:19]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=4[O:26][CH3:27])=[CH:18][N:17](S(C4C=CC(C)=CC=4)(=O)=O)[C:14]3=[N:15][CH:16]=2)[N:8]=[N:7][C:6]=1[NH2:38])=[O:4].CN(C)C=O.[OH-].[K+]>CO>[CH3:39][N:2]([CH3:1])[C:3]([C:5]1[CH:10]=[C:9]([C:11]2[CH:12]=[C:13]3[C:19]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=4[O:26][CH3:27])=[CH:18][NH:17][C:14]3=[N:15][CH:16]=2)[N:8]=[N:7][C:6]=1[NH2:38])=[O:4]

참가 물질

5

반응물 3

HCID 6228DimethylformamideHCID 14797Potassium HydroxideHCID 57731610HCID 57731610, 화합물

생성물 1

HCID 57731451HCID 57731451, 화합물수율 14.1%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

Crude 3-amino-6-[3-(2-methoxy-phenyl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-pyridazine-4-carboxylic acid dimethylamide (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 (0.5 mL). The mixture was carefully poured into saturated sodium bicarbonate and extracted with ethyl acetate. The organics were dried over sodium sulfate, filtered and dried to a residue which was purified by preparative HPLC to afford 3-amino-6-[3-(2-methoxy-phenyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-pyridazine-4-carboxylic acid dimethylamide (5.7 mg, 14.1%, 3 steps). 1H-NMR (500 MHz, dimethylsulfoxide-d6) δ 2.90 (s, 3H), 3.0 (s, 3H), 3.82 (s, 3H), 6.44 (s, 2H), 7.07 (dt, J=7.5 Hz, J=1.0 Hz, 1H), 7.13 (br d, J=7.5 Hz, 1H), 7.30 (dt, J=7.5 Hz, J=1.5 Hz, 1H), 7.61 (dd, J=7.5 Hz, J=2.0 Hz, 1H), 7.83 (d, J=2.5 Hz, 1H), 7.92 (s, 1H), 8.55 (d, J=2.0 Hz, 1H), 8.87 (d, J=2.5 Hz, 1H), 11.89 (s, 1H). MS: m/z 389 (M+H+).

후처리

  1. additionwas added
  2. customthe reaction was quenched by addition of acetic acid (0.5 mL)
  3. additionThe mixture was carefully poured into saturated sodium bicarbonate
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organics 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-6638841ca2f34d54beb5466f434d01eb
출처 데이터셋
uspto-grants-2010_05
특허 번호
US07709645B2

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