Sodium Methoxide → HCID 67503079, compound

HRID 1047025Notes

Reaction equation

HRID 1047025 reaction equation
Br[C:2]1[N:3]=[C:4]2[C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=3[NH:8][C:7]3[N:15]=[CH:16][CH:17]=[CH:18][C:6]=3[N:5]2[C:19]=1[C:20]1[CH:25]=[CH:24][C:23]([C:26]2([NH:30]C(=O)OC(C)(C)C)[CH2:29][CH2:28][CH2:27]2)=[CH:22][CH:21]=1.[CH3:38][O-:39].[Na+]>[Cu](I)I>[CH3:38][O:39][C:2]1[N:3]=[C:4]2[C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=3[NH:8][C:7]3[N:15]=[CH:16][CH:17]=[CH:18][C:6]=3[N:5]2[C:19]=1[C:20]1[CH:25]=[CH:24][C:23]([C:26]2([NH2:30])[CH2:27][CH2:28][CH2:29]2)=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 136331865tert-butyl {1-[4-(2-bromo-9H-imidazo[1,2-d]pyrido[2,3-b][1,4]benzodiazepin-3-yl)phenyl]cyclobutyl}carbamate

Product 1

HCID 67503079HCID 67503079, compoundYield 11%

Reagents, catalysts & solvents 1

HCID 83717Copper iodideCatalyst

Conditions

Temperature
100 °C

Procedure

A mixture of tert-butyl {1-[4-(2-bromo-9H-imidazo[1,2-d]pyrido[2,3-b][1,4]benzodiazepin-3-yl)phenyl]cyclobutyl}carbamate (50 mg, 0.09 mmol) and copper iodide (1.7 mg, 0.01 mmol) in sodium methoxide solution (1 M, 5 mL) was heated at 100° C. for 24 hour. After cooling to room temperature, the precipitate was collected and purified by HPLC to give the title compound as a white solid (5 mg, 11%).

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe precipitate was collected
  3. custompurified by HPLC

Sources & evidence

ORD record
ord-cb1ce2846b634ae9b4cfc2d8f86719b3
Source dataset
uspto-grants-2013_10
Patent number
US08569331B2

Reaction notes

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