Acetic Anhydride → HCID 117601884, compound

HRID 1773753Notes

Reaction equation

HRID 1773753 reaction equation
C(N(CC)CC)C.[C:8](OC(=O)C)(=[O:10])[CH3:9].[NH2:15][C:16]1[N:21]=[C:20]([C:22]([OH:46])([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][N:41]=2)[C:23]2[C:31]3[NH:30][C:29](=[O:32])[NH:28][C:27]=3[CH:26]=[C:25]([C:33]3[C:34]([CH3:39])=[N:35][O:36][C:37]=3[CH3:38])[CH:24]=2)[CH:19]=[CH:18][CH:17]=1>CN(C)C1C=CN=CC=1.CN(C)C=O>[C:8]([N:28]1[C:27]2[CH:26]=[C:25]([C:33]3[C:34]([CH3:39])=[N:35][O:36][C:37]=3[CH3:38])[CH:24]=[C:23]([C:22]([C:20]3[CH:19]=[CH:18][CH:17]=[C:16]([NH2:15])[N:21]=3)([OH:46])[C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][N:41]=3)[C:31]=2[NH:30][C:29]1=[O:32])(=[O:10])[CH3:9]

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 117601781HCID 117601781, compound

Product 1

HCID 117601884HCID 117601884, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

To a microwave vial capped with a septum, 4-(dimethylamino)pyridine (5.8 mg, 0.047 mmol) and triethylamine (9 μL, 0.07 mmol) in N,N-dimethylformamide (0.5 mL) were cooled to 0° C. in a nitrogen atmosphere. Acetic anhydride (4.4 μL, 0.047 mmol) was added and the reaction mixture was stirred for 15 minutes at 0° C. before a solution of 4-((6-aminopyridin-2-yl)(hydroxy)(pyridin-2-yl)methyl)-6-(3,5-dimethylisoxazol-4-yl)-1H-benzo[d]imidazol-2(3H)-one (10 mg, 0.023 mmol) in N,N-dimethylformamide (0.25 mL) was added dropwise to the reaction mixture. The reaction was allowed to warm to room temperature and stirred for thirty minutes (or until completion). The reaction was quenched with water and diluted with ethyl acetate. The organic layer was separated and saved and the organic layer was extracted with ethyl acetate (three times, 20 mL each). The organic fractions were collected, dried over MgSO4, filtered and concentrated. The product was isolated by preparatory HPLC to yield a clear oil.

Workup

  1. additionwas added dropwise to the reaction mixture
  2. temperatureto warm to room temperature
  3. customThe reaction was quenched with water
  4. additiondiluted with ethyl acetate
  5. customThe organic layer was separated
  6. extractionthe organic layer was extracted with ethyl acetate (three times, 20 mL each)
  7. customThe organic fractions were collected
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe product was isolated by preparatory HPLC
  12. customto yield a clear oil

Sources & evidence

ORD record
ord-464cbe6ebc2d4601ad8698fb2ba93bda
Source dataset
uspto-grants-2016_02
Patent number
US09255089B2

Reaction notes

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