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Cyanoacetamide → HCID 178452601, compound

HRID 1509120
Notes
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Reaction equation

HRID 1509120 reaction equation
[H-].[Na+].[C:3]([CH2:5][C:6]([NH2:8])=[O:7])#[N:4].[C:9]([O:13][C:14](=[O:39])[NH:15][C:16]1([C:20]2[CH:25]=[CH:24][C:23]([C:26](=O)/[C:27](/[C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)=[CH:28]/N(C)C)=[CH:22][CH:21]=2)[CH2:19][CH2:18][CH2:17]1)([CH3:12])([CH3:11])[CH3:10].CC(OCC1C2C(=CC=CC=2)C(COC(C)=O)=C2C=1C=CC=C2)=O>CN(C=O)C.CO.O>[C:9]([O:13][C:14](=[O:39])[NH:15][C:16]1([C:20]2[CH:21]=[CH:22][C:23]([C:26]3[C:27]([C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)=[CH:28][C:5]([C:3]#[N:4])=[C:6]([OH:7])[N:8]=3)=[CH:24][CH:25]=2)[CH2:17][CH2:18][CH2:19]1)([CH3:12])([CH3:10])[CH3:11]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 7898CyanoacetamideHCID 24758Sodium hydrideHCID 613145Acetic acid 10-acetoxymethyl-anthracen-9-ylmethyl esterHCID 66719110HCID 66719110, compound

Product 1

HCID 178452601HCID 178452601, compoundYield 93%

Reagents, catalysts & solvents 3

HCID 887
Methanol
Solvent
HCID 962WaterSolvent
HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
40 °C

Procedure

To a suspension of sodium hydride (3.58 g, 0.089 mol) in DMF (150 ml) at 0° C. was added a solution of 2-cyanoacetamide (3.48 g, 0.041 mol) and (E)-tert-butyl(1-(4-(3-(dimethylamino)-2-phenylacryloyl)phenyl)cyclobutyl)carbamate (15 g, 0.0357 mol) in methanol (5.5 ml) and DMF (150 ml). The resulting mixture was heated at 40° C. for 16 h. After cooled down to room temperature, the mixture was added to a solution of acetic (50 ml) in water (300 ml) slowly. The resulting precipitate was filtered and the filter cake was partitioned between water (250 ml) and dichloromethane (150 ml). The layers were separated and the aqueous phase extracted into dichloromethane (150 ml). The combined organic phases were washed with water (200 ml) and brine (150 ml), dried over Na2SO4, filtered and concentrated to dryness under reduced pressure to give the title compound as a yellow solid (14.6 g, 93%). LCMS (Method A): RT=6.59 min, M+1=442. 1H NMR (500 MHz, CDCl3): 7.89 (1H, s), 7.37-7.32 (2H, m), 7.22-7.16 (5H, m), 7.03-6.98 (2H, m), 2.50-2.37 (4H, m), 2.06-1.97 (1H, m), 1.82-1.77 (1H, m), 1.45-1.05 (9H, br).

Workup

  1. temperatureAfter cooled down to room temperature
  2. filtrationThe resulting precipitate was filtered
  3. customthe filter cake was partitioned between water (250 ml) and dichloromethane (150 ml)
  4. customThe layers were separated
  5. extractionthe aqueous phase extracted into dichloromethane (150 ml)
  6. washThe combined organic phases were washed with water (200 ml) and brine (150 ml)
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-049aa068019a4dde878053792b4f3822
Source dataset
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09221838B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes