Potassium Carbonate → 1-N-[10-chloro-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(8),2(6),9,11-tetraen-12-yl]cyclohexane-1,4-diamine

HRID 525093노트

반응식

HRID 525093 반응식
[Cl:1][C:2]1[N:13]=[C:12](Cl)[C:11]2[C:10]3[CH2:9][CH2:8][CH2:7][C:6]=3[S:5][C:4]=2[N:3]=1.[C@H:15]1([NH2:22])[CH2:20][CH2:19][C@H:18]([NH2:21])[CH2:17][CH2:16]1.C(=O)([O-])[O-].[K+].[K+]>CC#N.CCOC(C)=O>[Cl:1][C:2]1[N:13]=[C:12]([NH:21][CH:18]2[CH2:19][CH2:20][CH:15]([NH2:22])[CH2:16][CH2:17]2)[C:11]2[C:10]3[CH2:9][CH2:8][CH2:7][C:6]=3[S:5][C:4]=2[N:3]=1

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 127242292,4-Dichloro-6,7-dihydro-5h-cyclopenta[4,5]thieno[2,3-d]pyrimidineHCID 178511674HCID 178511674, 화합물

생성물 1

HCID 867623711-N-[10-chloro-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(8),2(6),9,11-tetraen-12-yl]cyclohexane-1,4-diamine수율 79%

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 8857Ethyl Acetate용매

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온도
80 °C

실험 절차

A 50-mL round-bottom flask placed a solution of 10,12-dichloro-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(8),2(6),9,11-tetraene (500 mg, 2.04 mmol, 1.00 equiv) in anhydrous CH3CN (20 mL) was added trans-cyclohexane-1,4-diamine (280 mg, 2.45 mmol, 1.20 equiv) and potassium carbonate (844 mg, 6.11 mmol, 3.00 equiv) at room temperature. The resulting solution was stirred overnight at 80° C. under nitrogen. The resulting solution was diluted with EtOAc, washed with brine, dried over anhydrous sodium sulfate and concentrated under vacuum. This resulted (520 mg, crude) of 1-N-[10-chloro-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(8),2(6),9,11-tetraen-12-yl]cyclohexane-1,4-diamine as a white solid which was used directly for next step without further purification.

후처리

  1. customA 50-mL round-bottom flask placed
  2. washwashed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under vacuum

출처 및 근거

ORD 기록
ord-841ca70298f04808b3a245d6f45109e3
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09340554B2

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