Potassium Phosphate, Tribasic → HCID 71585650, compound

HRID 526306Notes

Reaction equation

HRID 526306 reaction equation
[CH3:1][N:2]1[CH2:25][CH2:24][C:5]2=[C:6]([C:13]([C:15]3[CH:23]=[CH:22][C:18]([C:19]([OH:21])=O)=[CH:17][CH:16]=3)=[O:14])[C:7]3[C:12]([N:4]2[CH2:3]1)=[CH:11][CH:10]=[CH:9][CH:8]=3.C(N1C=CN=C1)(N1C=CN=C1)=O.[NH2:38][OH:39].Cl.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>CN(C=O)C.[Cl-].[Na+].O.CCN(CC)CC>[OH:39][NH:38][C:19](=[O:21])[C:18]1[CH:17]=[CH:16][C:15]([C:13]([C:6]2[C:7]3[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=3)[N:4]3[CH2:3][N:2]([CH3:1])[CH2:25][CH2:24][C:5]=23)=[O:14])=[CH:23][CH:22]=1

Participants

8

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 682631,1'-CarbonyldiimidazoleHCID 443297Hydroxyamine hydrochlorideHCID 89601990HCID 89601990, compound

Product 1

HCID 71585650HCID 71585650, compoundYield 16%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 4-(2-methyl-1,2,3,4-tetrahydropyrimido[1,6-a]indole-5-carbonyl)benzoic acid (60 mg) in 4 mL of DMF was added 100 mg of carbonyldiimidazole (CDI). The reaction mixture was stirred at 40° C. for 1 h and then treated with 280 mg of NH2OH.HCl, followed by 0.6 mL of Et3N. After stirring for 20 min at r.t., 5 mL of pH7 potassium phosphate buffer and 10 mL of brine were added and reaction mixture was extracted with 3×20 mL of EtOAc. The combined extracts were dried over Na2SO4, filtered, and the residue was purified by silica gel chromatography eluted with up to 10% MeOH/CH2Cl2 to give 10 mg of the title product as white solid.

Workup

  1. stirringAfter stirring for 20 min at r.t.
  2. customreaction mixture
  3. extractionwas extracted with 3×20 mL of EtOAc
  4. dry with materialThe combined extracts were dried over Na2SO4
  5. filtrationfiltered
  6. customthe residue was purified by silica gel chromatography
  7. washeluted with up to 10% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-847ee1a3c02447cb8ce6971357f7be5c
Source dataset
uspto-grants-2016_05
Patent number
US09345905B2

Reaction notes

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