Ammonia → HCID 68432063, compound

HRID 2092108Notes

Reaction equation

HRID 2092108 reaction equation
[Cl:1][C:2]1[C:7](=[O:8])[N:6]([CH2:9][C:10]([NH:12][CH:13]([CH2:17][CH3:18])[C:14]([OH:16])=O)=[O:11])[N:5]=[CH:4][C:3]=1[NH:19][C@@H:20]1[CH2:25][C@@H:24]2[CH2:26][C@@H:22]([C:23]2([CH3:28])[CH3:27])[C@H:21]1[CH3:29].[N:30]1(C(N2C=CN=C2)=O)C=CN=C1.N.O>CN(C)C=O>[Cl:1][C:2]1[C:7](=[O:8])[N:6]([CH2:9][C:10]([NH:12][CH:13]([CH2:17][CH3:18])[C:14]([NH2:30])=[O:16])=[O:11])[N:5]=[CH:4][C:3]=1[NH:19][C@@H:20]1[CH2:25][C@@H:24]2[CH2:26][C@@H:22]([C:23]2([CH3:27])[CH3:28])[C@H:21]1[CH3:29]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 962WaterHCID 682631,1'-CarbonyldiimidazoleHCID 68432311HCID 68432311, compound

Product 1

HCID 68432063HCID 68432063, compoundYield 29.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-({[5-Chloro-6-oxo-4-{[(1R,2R,3R,5S)-2,6,6-trimethylbicyclo[3.1.1]hept-3-yl]amino}pyridazin-1(6H)-yl]acetyl}amino)butyric acid (48 mg, 0.113 mmol) in N,N-dimethylformamide (2 mL) was stirred with di-1H-imidazolylmethanone (55 mg, 0.340 mmol) at room temperature for 2 days and then with 30% aqueous ammonia (0.2 mL) at room temperature for 5 hours. After completion of the reaction, the reaction solution was mixed with water and extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate) to give the desired product (14 mg, 29% yield).

Workup

  1. customAfter completion of the reaction
  2. extractionextracted with ethyl acetate
  3. dry with materialThe extract was dried over anhydrous magnesium sulfate
  4. customevaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-1594899aefa04cb88a52b0296307bf74
Source dataset
uspto-grants-2013_05
Patent number
US08440666B2

Reaction notes

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