Dimethylformamide dimethyl acetal → HCID 136343209, compound

HRID 2092118Notes

Reaction equation

HRID 2092118 reaction equation
[Cl:1][C:2]1[C:7](=[O:8])[N:6]([CH2:9][C:10]([NH2:12])=[O:11])[N:5]=[CH:4][C:3]=1[NH:13][C@@H:14]1[CH2:19][C@@H:18]2[CH2:20][C@@H:16]([C:17]2([CH3:22])[CH3:21])[C@H:15]1[CH3:23].CO[CH:26](OC)[N:27](C)C.[O:32]1[CH2:36]CCC1.O.Cl.CON>O1CCCC1.CN(C)C=O.O>[Cl:1][C:2]1[C:7](=[O:8])[N:6]([CH2:9][C:10]([NH:12]/[CH:26]=[N:27]\[O:32][CH3:36])=[O:11])[N:5]=[CH:4][C:3]=1[NH:13][C@@H:14]1[CH2:19][C@@H:18]2[CH2:20][C@@H:16]([C:17]2([CH3:22])[CH3:21])[C@H:15]1[CH3:23]

Participants

7

Reactant 4

HCID 78373Dimethylformamide dimethyl acetalHCID 521874O-Methylhydroxylamine hydrochlorideHCID 21881883Oxolane--water (1/1)HCID 68431472HCID 68431472, compound

Product 1

HCID 136343209HCID 136343209, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21974620tetrahydrofuran N,N-dimethylformamideSolvent

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]acetamide (32 mg, 0.0944 mmol) in tetrahydrofuran/N,N-dimethylformamide (1/0.1 mL) was stirred with 1,1-dimethoxy-N,N-dimethylmethanamine (25 μL, 0.188 mmol) at room temperature for 3 hours. The reaction solution was concentrated and stirred with tetrahydrofuran/water (1/2 mL) and methoxyamine hydrochloride (12 mg, 0.143 mmol) at room temperature for 2 hours. After completion of the reaction, the reaction solution was mixed with water and extracted with ethyl acetate, and the extract was dried over anhydrous magnesium sulfate and evaporated under reduced pressure to give the desired product (29 mg, 78% yield).

Workup

  1. concentrationThe reaction solution was concentrated
  2. customAfter completion of the reaction
  3. extractionextracted with ethyl acetate
  4. dry with materialthe extract was dried over anhydrous magnesium sulfate
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-a70fe4db4e354c09bc2c3a78b61847c9
Source dataset
uspto-grants-2013_05
Patent number
US08440666B2

Reaction notes

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