Cesium carbonate → HCID 131723668, 화합물

HRID 1825439노트

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HRID 1825439 반응식
CN(C)/[CH:3]=[C:4](\[C:15]1[NH:16][CH:17]=[CH:18][N:19]=1)/[C:5]([C:7]1[CH:12]=[CH:11][C:10]([C:13]#[N:14])=[CH:9][CH:8]=1)=O.Cl.[C:22]([NH:25][CH2:26][CH2:27][NH:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])(=[NH:24])[NH2:23].C([O-])([O-])=O.[Cs+].[Cs+]>CN1C(=O)CCC1>[C:32]([O:31][C:29]([NH:28][CH2:27][CH2:26][NH:25][C:22]1[N:23]=[C:5]([C:7]2[CH:8]=[CH:9][C:10]([C:13]#[N:14])=[CH:11][CH:12]=2)[C:4]([C:15]2[NH:19][CH:18]=[CH:17][N:16]=2)=[CH:3][N:24]=1)=[O:30])([CH3:35])([CH3:34])[CH3:33]

참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 693105754-[(2E)-3-(dimethylamino)-2-imidazolylprop-2-enoyl]benzenecarbonitrileHCID 178453692HCID 178453692, 화합물

생성물 1

HCID 131723668HCID 131723668, 화합물수율 83%

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone용매2회

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온도
100 °C

실험 절차

4-[(2E)-3-(dimethylamino)-2-imidazolylprop-2-enoyl]benzenecarbonitrile (8.0g, 30.0 mmol) in NMP (5 ml) was added to a stirred mixture of N-[2-(amidinoamino)ethyl](tert-butoxy)carboxamide, hydrochloride (13.8 g, 45 =mol)) and Cs2CO3 (11.72, 36.0 mmol) in NMP (15 ml). The reaction was heated to 100° C. for 48 hours. The reaction was followed by HPLC. Upon completion, the reaction was partitioned with water (50 ml) and dichloromethane (250 ml). The organic layer was separated and washed with water (2×50 ml), brine (50 ml), dried Na2SO4, filtered, and concentrated under reduced pressure. The product was purified by flash chromatography eluting with 10% methanol in dichloromethane. After stripping off the solvents and drying in vacuo, 10.08 g of (tert-butoxy)-N-(2-{[4-(4-cyanophenyl)-5-imidazolylpyrimidin-2-yl]amino}ethyl)carboxamide was obtained as a dark red glass in 83% yield.

후처리

  1. customUpon completion, the reaction was partitioned with water (50 ml) and dichloromethane (250 ml)
  2. customThe organic layer was separated
  3. washwashed with water (2×50 ml), brine (50 ml), dried Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe product was purified by flash chromatography
  7. washeluting with 10% methanol in dichloromethane
  8. customdrying in vacuo

출처 및 근거

ORD 기록
ord-71d5998592ba4600b9cdcfdf34562a07
출처 데이터셋
uspto-grants-2006_05
특허 번호
US07045519B2

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