Glycine → HCID 52947078, compound

HRID 733171Notes

Reaction equation

HRID 733171 reaction equation
O=[CH:2][CH2:3][CH2:4][C:5]1[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[CH:12]=2)[N:8]=[C:7]([C:21]#[N:22])[N:6]=1.[NH2:23][CH2:24][C:25]([OH:27])=[O:26].[OH2:28].C([BH3-])#N>CO.C(O)(=O)C>[F:18][C:17]([F:20])([F:19])[C:13]([OH:26])=[O:28].[C:25]([CH2:24][NH:23][CH2:2][CH2:3][CH2:4][C:5]1[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:19])([F:18])[F:20])[CH:12]=2)[N:8]=[C:7]([C:21]#[N:22])[N:6]=1)([OH:27])=[O:26].[C:25]([CH2:24][NH:23][CH2:2][CH2:3][CH2:4][C:5]1[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:19])([F:18])[F:20])[CH:12]=2)[N:8]=[C:7]([C:21]#[N:22])[N:6]=1)([OH:27])=[O:26]

Participants

8

Reactant 4

HCID 750GlycineHCID 962WaterHCID 498716Cyano-borohydrideHCID 86619632HCID 86619632, compound

Product 2

HCID 52947078HCID 52947078, compoundHCID 86619635HCID 86619635, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

To a stirred solution of 4-(3-oxo-propyl)-6-(3-trifluoromethylphenyl)-pyrimidine-2-carbonitrile (50 mg) in methanol (1 mL) was added glycine (25 mg), followed by water (100 μL) and acetic acid (12 μL). The mixture was stirred at room temperature for five minutes then solid supported cyanoborohydride (77 mg, 2.57 mmol/g) was added and stirring continued overnight. The reaction mixture was filtered and the filtrate concentrated under reduced pressure to yield crude product. Purification by preparative-HPLC afforded the TFA salt of 4-[3-(carboxymethyl-amino)-propyl]-6-(3-trifluoromethylphenyl)-pyrimidine-2-carbonitrile.

Workup

  1. additionwas added
  2. stirringstirring continued overnight
  3. filtrationThe reaction mixture was filtered
  4. concentrationthe filtrate concentrated under reduced pressure
  5. customto yield crude product
  6. customPurification

Sources & evidence

ORD record
ord-eefa024743b148929e036cd54d6b8433
Source dataset
uspto-grants-2009_09
Patent number
US07589095B2

Reaction notes

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