Ammonium Chloride → [6-(4,4-Dimethylcyclohexyl)-2-methylthieno[2,3-d]pyrimidin-4-yl](4-hydroxy-4-methylpiperidin-1-yl)methanone

HRID 2171828ノート

反応式

HRID 2171828 の反応式
[CH3:1][C:2]1([CH3:21])[CH2:7][CH2:6][CH:5]([C:8]2[S:20][C:11]3[N:12]=[C:13]([CH3:19])[N:14]=[C:15]([C:16](O)=[O:17])[C:10]=3[CH:9]=2)[CH2:4][CH2:3]1.[CH3:22][C:23]1([OH:29])[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[NH4+].[Cl-]>CN1C(=O)CCC1>[CH3:21][C:2]1([CH3:1])[CH2:7][CH2:6][CH:5]([C:8]2[S:20][C:11]3[N:12]=[C:13]([CH3:19])[N:14]=[C:15]([C:16]([N:26]4[CH2:27][CH2:28][C:23]([OH:29])([CH3:22])[CH2:24][CH2:25]4)=[O:17])[C:10]=3[CH:9]=2)[CH2:4][CH2:3]1

参加物

7

反応物 5

HCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 156491744-Methylpiperidin-4-olHCID 1180240036-(4,4-Dimethylcyclohexyl)-2-methylthieno[2,3-d]pyrimidine-4-carboxylic acid

生成物 1

HCID 118024018[6-(4,4-Dimethylcyclohexyl)-2-methylthieno[2,3-d]pyrimidin-4-yl](4-hydroxy-4-methylpiperidin-1-yl)methanone収率 60.6%

試薬・触媒・溶媒 1

HCID 13387N-methyl-2-pyrrolidone溶媒

実験手順

To a mixture of 6-(4,4-dimethylcyclohexyl)-2-methylthieno[2,3-d]pyrimidine-4-carboxylic acid (150 mg), 4-methylpiperidin-4-ol (68 mg), HATU (262 mg), and NMP (2.1 mL) was added DIPEA (244 μL), followed by stirring at room temperature overnight. To the reaction mixture was added a saturated aqueous NH4Cl solution, followed by extraction with EtOAc. The organic layer was washed sequentially with water and brine, dried over MgSO4, and then concentrated under reduced pressure. The residue was purified by silica gel column. The obtained purified product was suspended in IPE, collected by filtration, and then dried under reduced pressure to obtain [6-(4,4-dimethylcyclohexyl)-2-methylthieno[2,3-d]pyrimidin-4-yl](4-hydroxy-4-methylpiperidin-1-yl)methanone (120 mg).

後処理

  1. extractionfollowed by extraction with EtOAc
  2. washThe organic layer was washed sequentially with water and brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column
  6. customThe obtained purified product
  7. filtrationcollected by filtration
  8. customdried under reduced pressure

出典と根拠

ORDレコード
ord-6ef8702c37c84a5185de9292017b81d2
出典データセット
uspto-grants-2015_06
特許番号
US09051339B2

反応ノート

読み込み中…