Dimethylformamide → HCID 68768186, compound

HRID 2098581Notes

Reaction equation

HRID 2098581 reaction equation
[CH:1]1([NH:4][C:5](=[O:24])/[C:6](/[C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)=[CH:7]/[C:8]2[CH:16]=[CH:15][C:11]([C:12](O)=[O:13])=[CH:10][CH:9]=2)[CH2:3][CH2:2]1.CN(C=O)C.C1C=CC2N(O)N=NC=2C=1.[NH2:40][CH2:41][C:42]1[CH:53]=[CH:52][C:45]([CH:46]=[CH:47][C:48]([O:50][CH3:51])=[O:49])=[CH:44][CH:43]=1.C(N(CC)CC)C>O>[CH:1]1([NH:4][C:5](=[O:24])/[C:6](/[C:17]2[CH:18]=[CH:19][C:20]([F:23])=[CH:21][CH:22]=2)=[CH:7]/[C:8]2[CH:16]=[CH:15][C:11]([C:12]([NH:40][CH2:41][C:42]3[CH:43]=[CH:44][C:45]([CH:46]=[CH:47][C:48]([O:50][CH3:51])=[O:49])=[CH:52][CH:53]=3)=[O:13])=[CH:10][CH:9]=2)[CH2:3][CH2:2]1

Participants

7

Reactant 5

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 66927668HCID 66927668, compoundHCID 68771879HCID 68771879, compound

Product 1

HCID 68768186HCID 68768186, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a suspension of 4-((1E)-3-(cyclopropylamino)-2-(4-fluorophenyl)-3-oxoprop-1-en-1-yl)benzoic acid (0.3 g, 0.9 mmol, prepared according to the procedure described in Example 99, step-III) in DMF (5 mL) EDCl (0.35 g, 1.8 mmol), HOBt (0.12 g, 0.9 mmol), methyl 4-aminomethylcinnamate (0.237 g, 1.1 mmol), were added followed by triethylamine (0.4 mL, 3 mmol). The reaction mixture was stirred for 8 hours after which the mixture was poured to cold water (100 mL), the white precipitate formed was filtered, washed with water (1×150 mL), dried under vacuum to afford the title compound as a yellow solid (0.4 g, 87% yield).

Workup

  1. customprepared
  2. customthe white precipitate formed
  3. filtrationwas filtered
  4. washwashed with water (1×150 mL)
  5. customdried under vacuum

Sources & evidence

ORD record
ord-fe1f709782604bc18c036f037f5241a4
Source dataset
uspto-grants-2013_05
Patent number
US08450525B2

Reaction notes

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