Dichloromethane → N-((R)-1-(4-chloro-3-fluorophenyl)propyl)-2-((S)-1-hydroxybutan-2-ylamino)-5,6-dihydropyrido[3,4-d]pyrimidine-7(8H)-carboxamide

HRID 2279508노트

반응식

HRID 2279508 반응식
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([C@H:9]([NH2:12])[CH2:10][CH3:11])=[CH:5][C:4]=1[F:13].C(Cl)Cl.C1N=CN([C:22](N2C=NC=C2)=[O:23])C=1.Cl.[N:30]1[C:35]2[CH2:36][NH:37][CH2:38][CH2:39][C:34]=2[CH:33]=[N:32][C:31]=1[NH:40][C@@H:41]([CH2:44][CH3:45])[CH2:42][OH:43]>O>[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([C@H:9]([NH:12][C:22]([N:37]2[CH2:38][CH2:39][C:34]3[CH:33]=[N:32][C:31]([NH:40][C@@H:41]([CH2:44][CH3:45])[CH2:42][OH:43])=[N:30][C:35]=3[CH2:36]2)=[O:23])[CH2:10][CH3:11])=[CH:5][C:4]=1[F:13]

참가 물질

6

반응물 4

HCID 6344Dichloromethane2회HCID 682631,1'-CarbonyldiimidazoleHCID 68294121(S)-2-(5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-ylamino)butan-1-ol hydrochlorideHCID 86705486HCID 86705486, 화합물

생성물 1

HCID 60199018N-((R)-1-(4-chloro-3-fluorophenyl)propyl)-2-((S)-1-hydroxybutan-2-ylamino)-5,6-dihydropyrido[3,4-d]pyrimidine-7(8H)-carboxamide

시약·촉매·용매 1

HCID 962Water용매

실험 절차

To a solution of 139 (0.173 g, 0.773 mmol) and DCM (5 mL) at RT was added TEA (0.235 g, 2.32 mmol) and CDI (0.125 g, 0.773 mmol) and the reaction was stirred at RT for 30 min. To this solution was added dropwise a solution of 216 (0.200 g, 0.773 mmol), TEA (0.235 g, 2.32 mmol) and DCM (5 mL) and the resulting solution stirred for 4 h then poured into water and extracted with DCM. The combined organic fractions were dried (MgSO4), filtered, and concentrated in vacuo. The crude product was purified by SiO2 chromatography eluting with DCM/MeOH (500:40) to afford 0.050 g (14.8%) of I-57: MS m/z (APCI-pos) M+1=436.

후처리

  1. stirringthe resulting solution stirred for 4 h
  2. extractionextracted with DCM
  3. dry with materialThe combined organic fractions were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by SiO2 chromatography
  7. washeluting with DCM/MeOH (500:40)
  8. customto afford 0.050 g (14.8%) of I-57: MS m/z (APCI-pos) M+1=436

출처 및 근거

ORD 기록
ord-18404f1cbf124719a3ad580854ec1c55
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09133187B2

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