Glycine → HCID 23130657, compound

HRID 2080179Notes

Reaction equation

HRID 2080179 reaction equation
[NH2:1][CH2:2][C:3]([OH:5])=[O:4].N12CCCN=C1CCCCC2.[NH2:17][C:18]1[N:41]=[C:40](Cl)[CH:39]=[CH:38][C:19]=1[C:20]([NH:22][CH2:23][C:24]1[CH:29]=[CH:28][C:27]([O:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[CH:26][CH:25]=1)=[O:21]>CS(C)=O>[NH2:17][C:18]1[N:41]=[C:40]([NH:1][CH2:2][C:3]([OH:5])=[O:4])[CH:39]=[CH:38][C:19]=1[C:20](=[O:21])[NH:22][CH2:23][C:24]1[CH:29]=[CH:28][C:27]([O:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 750GlycineHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 231305612-Amino-6-chloro-N-(4-benzyloxy-benzyl)-nicotinamide

Product 1

HCID 23130657HCID 23130657, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
130 °C

Procedure

Glycine (935 mg, 12.5 mmol) and 1,8-diazabicyclo[5,4,0]undec-7-ene (1.86 mL, 12.5 mmol) were added to 2-amino-N-(4-benzyloxy-benzyl)-6-chloro-nicotinamide described in Preparation Example A+-18 (454 mg, 1.25 mmol) under nitrogen atmosphere, and the solution was stirred for 6 hours at 130° C. Dimethylsulfoxide (35 mL) was added to the reaction mixture, which was then filtered with polytetrafluoroethylene membrane filter (Whatman Inc), the filtrate was purified by reverse phase high performance liquid chromatography (acetonitrile-water mobile phase (containing 0.1% trifluoroacetic acid) was used), and the title compound (287 mg, 0.551 mmol, 44%) was obtained.

Workup

  1. filtrationwas then filtered with polytetrafluoroethylene membrane
  2. filtrationfilter (Whatman Inc)
  3. customthe filtrate was purified by reverse phase high performance liquid chromatography (acetonitrile-water mobile phase (containing 0.1% trifluoroacetic acid) was used)

Sources & evidence

ORD record
ord-653d642946ba4c17b321b45a9ef01a27
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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