(1,1'-Biphenyl)-4-carboxylic acid → HCID 11628130, compound

HRID 1441280Notes

Reaction equation

HRID 1441280 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:24])=[C:6]([N:8]2[CH2:17][C:16]3[C:11](=[N:12][C:13]([S:18]([CH3:21])(=[O:20])=[O:19])=[N:14][CH:15]=3)[N:10]([CH3:22])[C:9]2=[O:23])[CH:7]=1.[C:25]1([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH:30]=[CH:29][C:28]([C:31](O)=[O:32])=[CH:27][CH:26]=1.CCN=C=NCCCN(C)C.Cl>ClCCl.CN(C)C1C=CN=CC=1>[Cl:24][C:5]1[CH:4]=[CH:3][C:2]([NH:1][C:31]([C:28]2[CH:29]=[CH:30][C:25]([C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=3)=[CH:26][CH:27]=2)=[O:32])=[CH:7][C:6]=1[N:8]1[CH2:17][C:16]2[C:11](=[N:12][C:13]([S:18]([CH3:21])(=[O:19])=[O:20])=[N:14][CH:15]=2)[N:10]([CH3:22])[C:9]1=[O:23]

Participants

6

Reactant 3

HCID 66724(1,1'-Biphenyl)-4-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 68700878HCID 68700878, compound

Product 1

HCID 11628130HCID 11628130, compoundYield 28%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

0.2 g 3-(5-Amino-2-chloro-phenyl)-7-methanesulfonyl-1-methyl-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one were dissolved in 50 mL of dichloromethane. 0.137 g Biphenyl-4-carboxylic acid and 0.042 g 4-dimethylaminopyridine (DMAP) were added. The solution was cooled to 0° C. and 0.128 g N-(3-dimethylaminopropyl)-N-ethylcarbodiimide hydrochloride (EDCl), dissolved in 20 mL dichloromethane were slowly added. The reaction mixture was stirred for 24 h under nitrogen. The reaction was quenched by extraction with 100 mL of an aqueous solution of potassium carbonate. The phases were separated, the aqueous phase was extracted with dichloromethane, and the combined organic phases were dried over sodium sulfate and evaporated. The crude product was purified by flash chromatography on silica gel (n-heptane/ethyl acetate (EtOAc)) to give the title product in 28% yield.

Workup

  1. additionwere slowly added
  2. customThe reaction was quenched by extraction with 100 mL of an aqueous solution of potassium carbonate
  3. customThe phases were separated
  4. extractionthe aqueous phase was extracted with dichloromethane
  5. dry with materialthe combined organic phases were dried over sodium sulfate
  6. customevaporated
  7. customThe crude product was purified by flash chromatography on silica gel (n-heptane/ethyl acetate (EtOAc))

Sources & evidence

ORD record
ord-3ecdf53190b84dd199f6172d58ff35e4
Source dataset
uspto-grants-2010_02
Patent number
US07655651B2

Reaction notes

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