Acetic Acid → HCID 69050401, compound

HRID 733170Notes

Reaction equation

HRID 733170 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.Cl.[CH3:24][NH:25][C:26](=[O:29])[CH2:27][NH2:28].C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[CH3:48][OH:49]>>[F:18][C:17]([F:20])([F:19])[C:48]([OH:29])=[O:49].[CH3:24][NH:25][C:26]([CH2:27][NH:28][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:20])([F:19])[F:18])[CH:12]=2)[N:8]=[C:7]([C:21]#[N:22])[N:6]=1)=[O:29].[CH3:24][NH:25][C:26]([CH2:27][NH:28][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:20])([F:19])[F:18])[CH:12]=2)[N:8]=[C:7]([C:21]#[N:22])[N:6]=1)=[O:29]

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 887MethanolHCID 5049666Sodium triacetoxyborohydrideHCID 138422022-amino-N-methylacetamide hydrochlorideHCID 86619632HCID 86619632, compound

Product 2

HCID 69050401HCID 69050401, compoundHCID 86619634HCID 86619634, compound

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 methyl amide hydrochloride (41 mg) and acetic acid (12 μL). The mixture was stirred for 5 minutes then sodium triacetoxy borohydride (42 mg) was added and stirring was continued at room temperature overnight. Methanol was removed in vacuo and the resulting residue dissolved in DCM (20 mL) and washed with saturated sodium bicarbonate and water (1:1, 2×20 mL). The organic layer was separated, dried over sodium sulphate and evaporated to yield crude product as an oil. Purification by preparative-HPLC afforded the TFA salt of 4-[3-(methylcarbamoylmethyl-amino)-propyl]-6-(3-trifluoromethylphenyl)-pyrimidine-2-carbonitrile as a white solid (13 mg).

Workup

  1. stirringstirring
  2. waitwas continued at room temperature overnight
  3. customMethanol was removed in vacuo
  4. dissolutionthe resulting residue dissolved in DCM (20 mL)
  5. washwashed with saturated sodium bicarbonate and water (1:1, 2×20 mL)
  6. customThe organic layer was separated
  7. dry with materialdried over sodium sulphate
  8. customevaporated
  9. customto yield crude product as an oil
  10. customPurification

Sources & evidence

ORD record
ord-9977c71acfff48a3b888c68705dfd910
Source dataset
uspto-grants-2009_09
Patent number
US07589095B2

Reaction notes

Loading…