Methanol → HCID 71240866, 화합물

HRID 1842715노트

반응식

HRID 1842715 반응식
Cl[C:2]1[N:7]=[C:6]([C:8]2[CH:9]=[N:10][N:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=23)[C:5]([Cl:17])=[CH:4][N:3]=1.[CH3:18][O:19][C:20]1[CH:26]=[C:25]([C:27]2[CH2:28][CH2:29][N:30]([CH3:33])[CH2:31][CH:32]=2)[C:24]([N+:34]([O-:36])=[O:35])=[CH:23][C:21]=1[NH2:22].C[Si]([N-][Si](C)(C)C)(C)C.[Li+].CO>C1COCC1>[Cl:17][C:5]1[C:6]([C:8]2[CH:9]=[N:10][N:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=23)=[N:7][C:2]([NH:22][C:21]2[CH:23]=[C:24]([N+:34]([O-:36])=[O:35])[C:25]([C:27]3[CH2:32][CH2:31][N:30]([CH3:33])[CH2:29][CH:28]=3)=[CH:26][C:20]=2[O:19][CH3:18])=[N:3][CH:4]=1

참가 물질

6

반응물 4

HCID 887MethanolHCID 2733832Lithium HexamethyldisilazideHCID 592911623-(2,5-Dichloropyrimidin-4-yl)pyrazolo[1,5-a]pyridine2회HCID 866773252-methoxy-4-(1-methyl-3,6-dihydro-2H-pyridin-4-yl)-5-nitroaniline2회

생성물 1

HCID 71240866HCID 71240866, 화합물수율 72.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A mixture of 3-(2,5-dichloropyrimidin-4-yl)pyrazolo[1,5-a]pyridine (Intermediate 21, 575 mg, 1.86 mmol) and 2-methoxy-4-(1-methyl-3,6-dihydro-2H-pyridin-4-yl)-5-nitroaniline (Intermediate 3, 490 mg, 1.86 mmol) was stirred in THF (30 mL) and cooled in an ice/water bath. Lithium bis(trimethylsilyl)amide (4.10 mL, 4.10 mmol, 1M in THF) was then added dropwise and the mixture was stirred for 1 h. CH3OH was added and the mixture was concentrated in vacuo. The crude material was suspended in CH3OH and the mixture was filtered. The collected solid was washed with CH3OH and diethyl ether and dried on the filter to give the title compound (660 mg, 72%) as a yellow powder; 1H NMR: 2.29 (3H, s), 2.30-2.38 (2H, m), 2.58 (2H, t), 2.97 (2H, dd), 3.96 (3H, s), 5.60-5.68 (1H, m), 7.00 (1H, s), 7.16 (1H, td), 7.36-7.45 (1H, m), 8.49-8.56 (3H, m), 8.87 (1H, d), 8.90 (1H, s), 8.97 (1H, s); m/z: ES+ MH+ 492.4.

후처리

  1. temperaturecooled in an ice/water bath
  2. concentrationthe mixture was concentrated in vacuo
  3. filtrationthe mixture was filtered
  4. washThe collected solid was washed with CH3OH and diethyl ether
  5. customdried on the
  6. filtrationfilter

출처 및 근거

ORD 기록
ord-a9ae075771974ec0b1d79ebe15e991bf
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08946235B2

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