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 2279508ノート

反応式

HRID 2279508 の反応式
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]

参加物

6

反応物 4

HCID 6344Dichloromethane2 回HCID 682631,1'-CarbonyldiimidazoleHCID 68294121(S)-2-(5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-ylamino)butan-1-ol hydrochlorideHCID 86705486HCID 86705486、化合物

生成物 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

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-18404f1cbf124719a3ad580854ec1c55
出典データセット
uspto-grants-2015_09
特許番号
US09133187B2

反応ノート

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