Sodium triacetoxyborohydride → 4-{1-[2-Chloro-6-morpholin-4-yl-9-(tetrahydropyran-2-yl)-9H-purin-8-ylmethyl]azetidin-3-yl}piperazin-2-one

HRID 1945671ノート

反応式

HRID 1945671 の反応式
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[C:7]([CH:17]=O)[N:8]2[CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][O:12]2)=[C:4]([N:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)[N:3]=1.[NH:25]1[CH2:28][CH:27]([N:29]2[CH2:34][CH2:33][NH:32][C:31](=[O:35])[CH2:30]2)[CH2:26]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.CN(C=O)C>[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[C:7]([CH2:17][N:25]3[CH2:26][CH:27]([N:29]4[CH2:34][CH2:33][NH:32][C:31](=[O:35])[CH2:30]4)[CH2:28]3)[N:8]2[CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][O:12]2)=[C:4]([N:19]2[CH2:20][CH2:21][O:22][CH2:23][CH2:24]2)[N:3]=1

参加物

6

反応物 3

HCID 5049666Sodium triacetoxyborohydrideHCID 596034642-chloro-6-morpholin-4-yl-9-(tetrahydropyran-2-yl)-9H-purine-8-carbaldehydeHCID 596061454-(Azetidin-3-yl)piperazin-2-one

生成物 1

HCID 596060104-{1-[2-Chloro-6-morpholin-4-yl-9-(tetrahydropyran-2-yl)-9H-purin-8-ylmethyl]azetidin-3-yl}piperazin-2-one収率 67.5%

試薬・触媒・溶媒 2

HCID 111,2-Dichloroethane溶媒HCID 6228Dimethylformamide溶媒

実験手順

A mixture of 2-chloro-6-morpholin-4-yl-9-(tetrahydropyran-2-yl)-9H-purine-8-carbaldehyde (1.06 g, 3.01 mmol) and 4-azetidin-3-ylpiperazin-2-one (560 mg, 3.61 mmol) in DCE (60 mL) and DMF (20 mL) was allowed to stir at r.t. for 10 min before the addition of 4 Å powdered molecular sieves (3.0 g) followed by sodium triacetoxyborohydride (1.28 g, 6.04 mmol). The resulting mixture was allowed to stir for 64 h then filtered through Celite® which was washed with DCM. The filtrate was concentrated in vacuo and the resulting residue dissolved in EtOAc and washed with NaHCO3, H2O and brine. The organic phase was dried (Na2SO4) and concentrated in vacuo affording the title compound as a yellow gum (997 mg, 67%). LCMS (method A): RT 2.19 and 2.11 min [M−C5H9O+H]+407.3

後処理

  1. stirringto stir for 64 h
  2. filtrationthen filtered through Celite® which
  3. washwas washed with DCM
  4. concentrationThe filtrate was concentrated in vacuo
  5. dissolutionthe resulting residue dissolved in EtOAc
  6. washwashed with NaHCO3, H2O and brine
  7. dry with materialThe organic phase was dried (Na2SO4)
  8. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-551295f77a784574aba574f40ffb9c50
出典データセット
uspto-grants-2013_03
特許番号
US08394796B2

反応ノート

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