Ammonia → HCID 66751648, compound

HRID 1182825Notes

Reaction equation

HRID 1182825 reaction equation
[CH2:1]([C:5]1[N:6]=[C:7]([CH3:38])[N:8]([C:27]2[N:32]=[CH:31][C:30]([O:33][CH2:34][C:35](O)=[O:36])=[CH:29][N:28]=2)[C:9](=[O:26])[C:10]=1[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[C:24]#[N:25])=[CH:14][CH:13]=1)[CH2:2][CH2:3][CH3:4].Cl.C([N:42]=C=NCCCN(C)C)C.O.ON1C2C=CC=CC=2N=N1.N>O.ClCCl>[CH2:1]([C:5]1[N:6]=[C:7]([CH3:38])[N:8]([C:27]2[N:28]=[CH:29][C:30]([O:33][CH2:34][C:35]([NH2:42])=[O:36])=[CH:31][N:32]=2)[C:9](=[O:26])[C:10]=1[CH2:11][C:12]1[CH:13]=[CH:14][C:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[C:24]#[N:25])=[CH:16][CH:17]=1)[CH2:2][CH2:3][CH3:4]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 86762287HCID 86762287, compound

Product 1

HCID 66751648HCID 66751648, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Process 2: The dichloromethane (3 mL) solution of 2-{2-[4-butyl-5-[(2′-cyanobiphenyl-4-yl)methyl]-2-methyl-6-oxopyrimidin-1(6H)-yl]pyrimidin-5-yl oxy}acetic acid (51 mg, 0.1 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride salt (29 mg, 0.15 mmol) and 1-hydroxybenzotriazol-hydrate (21 mg, 0.15 mmol) was stirred at room temperature for 1 hr. Ammonia (28% aqueous solution, 0.5 mL) was added thereto and stirred at room temperature for 4 hrs. The reaction mixture was added water and extracted with chloroform. The organic layer was combined, washed with water and brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The resulting residues were subjected to silica gel column chromatography (chloroform/methanol) to obtain 2-{2-{4-butyl-5-[(2′-cyanobiphenyl-4-yl)methyl]-2-methyl-6-oxopyrimidin-1(6H)-yl}pyrimidin-5-yl oxy}acetamide (35 mg, 69%) as a colorless and transparent oil.

Workup

  1. extractionextracted with chloroform
  2. washwashed with water and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4351f1cdf7e94178aa01f4d33d641629
Source dataset
uspto-grants-2014_03
Patent number
US08664226B2

Reaction notes

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