Phenyl isocyanate → HCID 178521958, 화합물

HRID 2203274노트

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HRID 2203274 반응식
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:22][N:12]3[C:13](=[O:21])[NH:14][C:15]4[CH:16]=[CH:17][CH:18]=[CH:19][C:20]=4[C:11]3=[N:10][CH2:9]2)=[CH:4][CH:3]=1.[C:23]1([N:29]=[C:30]=[O:31])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C1COCC1>[O:21]=[C:13]1[N:12]2[CH2:22][CH:8]([C:5]3[CH:6]=[CH:7][C:2]([NH:1][C:30]([NH:29][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)=[O:31])=[CH:3][CH:4]=3)[CH2:9][N:10]=[C:11]2[C:20]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[NH:14]1

참가 물질

4

반응물 2

HCID 7672Phenyl isocyanateHCID 178507413HCID 178507413, 화합물

생성물 1

HCID 178521958HCID 178521958, 화합물수율 71%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a mixture of 3-(4-aminophenyl)-2,3,4,7-tetrahydro-6H-pyrimido[1,2-c]quinazolin-6-one (25.1 mg, 0.086 mmol) in 1.1 mL THF was added phenyl isocyanate (0.0103 mL, 0.095 mmol) and the reaction stirred at rt. After 45 min, the reaction was briefly warmed to approximately 50° C. and then allowed to cool to rt. At 2.5 hours the reaction was quenched with MeOH, evaporated, then triturated with MeOH, EtOAc, and then 50% EtOAc/hexane to give the title compound as a light tan solid (25.0 mg, 71%). 1H NMR (DMSO-d6) δ: 10.69 (br. s, 1H), 8.64 (br. s, 2H), 7.98 (d, J=7.0 Hz, 1H), 7.40-7.47 (m, 5H), 7.21-7.31 (m, 4H), 6.92-7.10 (m, 3H), 4.18-4.26 (m, 1H), 3.67-3.77 (m, 1H), 3.49-3.61 (m, 2H), 2.89-3.03 (m, 1H).

후처리

  1. temperaturethe reaction was briefly warmed to approximately 50° C.
  2. temperatureto cool to rt
  3. customAt 2.5 hours the reaction was quenched with MeOH
  4. customevaporated
  5. customtriturated with MeOH, EtOAc

출처 및 근거

ORD 기록
ord-997986b5309c4143980cf3e76353fa0b
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09365575B2

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