Glycolic Acid → HCID 67095296、化合物

HRID 1471821ノート

反応式

HRID 1471821 の反応式
[O:1]([C:8]1[CH:13]=[CH:12][C:11]([C:14]2[C:22]3[C:17](=[N:18][CH:19]=[N:20][C:21]=3[NH2:23])[N:16]([C@@H:24]3[CH2:29][CH2:28][CH2:27][NH:26][CH2:25]3)[N:15]=2)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:30](O)(=[O:33])[CH2:31][OH:32].C(N(CC)CC)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C1COCC1>[NH2:23][C:21]1[N:20]=[CH:19][N:18]=[C:17]2[N:16]([C@@H:24]3[CH2:29][CH2:28][CH2:27][N:26]([C:31](=[O:32])[CH2:30][OH:33])[CH2:25]3)[N:15]=[C:14]([C:11]3[CH:10]=[CH:9][C:8]([O:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)=[CH:13][CH:12]=3)[C:22]=12

参加物

6

反応物 4

HCID 757Glycolic AcidHCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 582232723-(4-Phenoxy-phenyl)-1-piperidin-3-yl-1H-pyrazolo[3,4-d]pyriMidin-4-ylaMine

生成物 1

HCID 67095296HCID 67095296、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a mixture of (R)-3-(4-phenoxyphenyl)-1-(piperidin-3-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (6) (38.62 g), glycolic acid (9.13 g) and triethylamine (27.90 mL) in THF (500 mL) stirring in an ice bath, was added HATU (45.63 g) in one portion. The reaction was allowed to warm up to room temperature and stirred overnight (16 hrs). Solvent was removed by rotoevaporation. The residue was diluted with dichloromethane (500 mL), washed with aqueous NaOH solution (10%, 300 mL). The solid was filtered off and the bi-layer system was separated. The organic layer was washed with brine, dried (Na2SO4), filtered and evaporated in vacuo. The residue was triturated with acetonitrile (300 mL) with some heating and cooled to room temperature. The mixture was filtered after sitting at room temperature overnight (16 hrs) and filtered. The solid collected was washed with small amount of acetonitrile and dried under high vacuo to provide the title compound a white powder with slight pink color (34.8 g).

後処理

  1. stirringstirred overnight (16 hrs)
  2. customSolvent was removed by rotoevaporation
  3. additionThe residue was diluted with dichloromethane (500 mL)
  4. washwashed with aqueous NaOH solution (10%, 300 mL)
  5. filtrationThe solid was filtered off
  6. customthe bi-layer system was separated
  7. washThe organic layer was washed with brine
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered
  10. customevaporated in vacuo
  11. customThe residue was triturated with acetonitrile (300 mL) with some heating and
  12. temperaturecooled to room temperature
  13. filtrationThe mixture was filtered
  14. filtration(16 hrs) and filtered
  15. customThe solid collected
  16. washwas washed with small amount of acetonitrile
  17. customdried under high vacuo

出典と根拠

ORDレコード
ord-55c236c1d3084c8fbba656489ac31e6c
出典データセット
uspto-grants-2015_04
特許番号
US09012463B2

反応ノート

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