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Potassium Carbonate → 4-[((2S)-2-Amino-3-{7-[2-(1H-pyrrol-1-yl)ethyl]-9-oxa-3,7-diazabicyclo[3.3.1]non-3-yl}propyl)oxy]benzonitrile

HRID 1374119
ノート
印刷プレビュー

反応式

HRID 1374119 の反応式
[C:1]([C:3]1[CH:29]=[CH:28][C:6]([O:7][CH2:8][C@@H:9]([NH:20]C(=O)OC(C)(C)C)[CH2:10][N:11]2[CH2:18][CH:17]3[O:19][CH:13]([CH2:14][NH:15][CH2:16]3)[CH2:12]2)=[CH:5][CH:4]=1)#[N:2].Br[CH2:31][CH2:32][N:33]1[CH:37]=[CH:36][CH:35]=[CH:34]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[NH2:20][C@@H:9]([CH2:10][N:11]1[CH2:18][CH:17]2[O:19][CH:13]([CH2:14][N:15]([CH2:31][CH2:32][N:33]3[CH:37]=[CH:36][CH:35]=[CH:34]3)[CH2:16]2)[CH2:12]1)[CH2:8][O:7][C:6]1[CH:28]=[CH:29][C:3]([C:1]#[N:2])=[CH:4][CH:5]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 116512251-(2-Bromoethyl)pyrroleHCID 86588969tert-butyl (1S)-2-(4-cyanophenoxy)-1-(9-oxa-3,7-diaza-bicyclo[3.3.1]non-3-ylmethyl)ethylcarbamate

生成物 1

HCID 684557444-[((2S)-2-Amino-3-{7-[2-(1H-pyrrol-1-yl)ethyl]-9-oxa-3,7-diazabicyclo[3.3.1]non-3-yl}propyl)oxy]benzonitrile収率 90.7%

試薬・触媒・溶媒 1

HCID 6228
Dimethylformamide
溶媒

実験手順

A mixture of tert-butyl (1S)-2-(4-cyanophenoxy)-1-(9-oxa-3,7-diaza-bicyclo[3.3.1]non-3-ylmethyl)ethylcarbamate (Preparation J; 100.62 mg, 0.25 mmol), 1-(2-bromoethyl)pyrrole (52.21 mg, 0.30 mmol) and TEA (37.9 mg, 0.375 mmol) in DMF (2.5 mL) was stirred at rt for 2 days and then at 50° C. for 1 day. The solvent was evaporated and the resulting residue dissolved in ethyl acetate (0.5 mL). Ethyl acetate saturated with gaseous hydrochloric acid (2 mL) was added, and the reaction mixture stirred for 1.5 h at rt. The solvent was evaporated and the resulting residue dissolved in a mixture of MeCN (2.5 mL) and H2O (0.13 mL). Potassium carbonate (100 mg, 0.72 mmol) was added, and the mixture stirred overnight at rt. The mixture was filtered and the filtrate concentrated in vacuo. The resulting crude product was dissolved in DCM (2 mL), which solution was added to a ion-exchange solid-phase extraction plug (CBA, 2 g). After 80 min, the product was eluted with DCM:MeCN (4×2 mL of 4:1), followed by DCM:MeOH:TEA (8:1:1), to give 89.7 mg (90.7%) of the title compound.

後処理

  1. waitat 50° C. for 1 day
  2. customThe solvent was evaporated
  3. dissolutionthe resulting residue dissolved in ethyl acetate (0.5 mL)
  4. additionEthyl acetate saturated with gaseous hydrochloric acid (2 mL) was added
  5. stirringthe reaction mixture stirred for 1.5 h at rt
  6. customThe solvent was evaporated
  7. dissolutionthe resulting residue dissolved in a mixture of MeCN (2.5 mL) and H2O (0.13 mL)
  8. stirringthe mixture stirred overnight at rt
  9. filtrationThe mixture was filtered
  10. concentrationthe filtrate concentrated in vacuo
  11. dissolutionThe resulting crude product was dissolved in DCM (2 mL)
  12. additionwhich solution was added to a ion-exchange solid-phase extraction plug (CBA, 2 g)
  13. waitAfter 80 min
  14. washthe product was eluted with DCM

出典と根拠

ORDレコード
ord-1e651fd6de3f4ef7a6c915f051ab9dc6
出典データセット
uspto-grants-2007_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07164017B2

反応ノート

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