Dichloromethane → N-((S)-2-(tert-butyldimethylsilyloxy)-1-(3,4-dichlorophenyl)ethyl)-2-(1,1,1-trifluoropropan-2-ylamino)-5,6-dihydropyrido[3,4-d]pyrimidine-7(8H)-carboxamide

HRID 2279539노트

반응식

HRID 2279539 반응식
[Si:1]([O:8][CH2:9][C@H:10]([C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[C:14](F)[CH:13]=1)[NH2:11])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C(Cl)[Cl:21].C1N=CN([C:28](N2C=NC=C2)=[O:29])C=1.[F:35][C:36]([F:51])([F:50])[CH:37]([NH:39][C:40]1[N:41]=[CH:42][C:43]2[CH2:49][CH2:48][NH:47][CH2:46][C:44]=2[N:45]=1)[CH3:38]>O>[Si:1]([O:8][CH2:9][C@@H:10]([NH:11][C:28]([N:47]1[CH2:48][CH2:49][C:43]2[CH:42]=[N:41][C:40]([NH:39][CH:37]([CH3:38])[C:36]([F:35])([F:50])[F:51])=[N:45][C:44]=2[CH2:46]1)=[O:29])[C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([Cl:21])[CH:13]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

참가 물질

6

반응물 4

HCID 6344Dichloromethane2회HCID 682631,1'-CarbonyldiimidazoleHCID 68294199N-(1,1,1-trifluoropropan-2-yl)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-amineHCID 86705474(S)-2-(tert-butyldimethylsilyloxy)-1-(4-chloro-3-fluorophenyl)ethanamine

생성물 1

HCID 68294705N-((S)-2-(tert-butyldimethylsilyloxy)-1-(3,4-dichlorophenyl)ethyl)-2-(1,1,1-trifluoropropan-2-ylamino)-5,6-dihydropyrido[3,4-d]pyrimidine-7(8H)-carboxamide수율 83.1%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

To a solution of 85 (0.104 g, 0.325 mmol) and DCM (5 mL) at RT was added TEA (0.136 mL, 0.975 mmol) and CDI (0.0527 g, 0.325 mmol) and the reaction was stirred at RT for 30 min and then added to a solution of 300 (0.080 g, 0.325 mmol), TEA (0.136 ml, 0.975 mmol) and DCM (5 mL) solution and the resulting solution stirred for 4 h. The reaction mixture was poured into water and extracted with DCM. The combined organic extracts were dried (MgSO4), filtered, and concentrated in vacuo. The crude product was purified by SiO2 chromatography eluting with DCM/MeOH (500:7) to afford 0.160 g (83.1%) of N—((S)-2-(tert-butyldimethylsilyloxy)-1-(3,4-dichlorophenyl)ethyl)-2-(1,1,1-trifluoropropan-2-ylamino)-5,6-dihydropyrido[3,4-d]pyrimidine-7(8H)-carboxamide (302).

후처리

  1. stirringthe resulting solution stirred for 4 h
  2. extractionextracted with DCM
  3. dry with materialThe combined organic extracts were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by SiO2 chromatography
  7. washeluting with DCM/MeOH (500:7)

출처 및 근거

ORD 기록
ord-86149794adf04f6ba2bde03f2489b710
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09133187B2

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