Dimethylformamide → HCID 68767568, compound

HRID 2098572Notes

Reaction equation

HRID 2098572 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5](/[C:8](/[C:21]([NH:23][CH:24]2[CH2:26][CH2:25]2)=[O:22])=[CH:9]\[C:10]2[CH:15]=[CH:14][C:13]([CH:16]=[CH:17][C:18](O)=[O:19])=[CH:12][CH:11]=2)=[CH:4][CH:3]=1.CN(C=O)C.C1C=CC2N(O)N=NC=2C=1.Cl.[CH3:43][O:44][C:45](=[O:54])[C:46]1[CH:51]=[CH:50][C:49]([CH2:52][NH2:53])=[CH:48][CH:47]=1.C(N(CC)CC)C>O>[CH:24]1([NH:23][C:21](=[O:22])/[C:8](/[C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)=[CH:9]/[C:10]2[CH:15]=[CH:14][C:13]([CH:16]=[CH:17][C:18]([NH:53][CH2:52][C:49]3[CH:50]=[CH:51][C:46]([C:45]([O:44][CH3:43])=[O:54])=[CH:47][CH:48]=3)=[O:19])=[CH:12][CH:11]=2)[CH2:25][CH2:26]1

Participants

7

Reactant 5

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 2729253Methyl 4-(aminomethyl)benzoate hydrochlorideHCID 68424066HCID 68424066, compound

Product 1

HCID 68767568HCID 68767568, compoundYield 53.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a suspension of (1E)-3-(4-(2-(4-fluorophenyl)-3-(cyclopropylamino)-3-oxoprop-1-en-1-yl)phenyl)acrylic acid (prepared according to the procedure described in Example 59, step-II, 0.35 g, 1 mmol) in DMF (15 mL) EDCI (0.83 g, 2 mmol), HOBt (0.13 g, 1 mmol) and methyl-4-aminomethylbenzoate hydrochloride salt (0.18 g, 0.9 mmol), were added, followed by triethylamine (0.4 mL, 3 mmol). The reaction mixture was stirred at room temperature for 1.5 hours, after which the mixture was added to cold water (50 mL). The aqueous layer was extracted with ethyl acetate (1×150 mL) and washed with water (2×50 mL), 10% dilute HCl (50 mL) and brine (1×100 mL). The organic layer was dried over anhydrous Na2SO4 and concentrated to give the crude compound (0.225 g, 53.5% yield).

Workup

  1. customprepared
  2. extractionThe aqueous layer was extracted with ethyl acetate (1×150 mL)
  3. washwashed with water (2×50 mL), 10% dilute HCl (50 mL) and brine (1×100 mL)
  4. dry with materialThe organic layer was dried over anhydrous Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-3853bd9cc8774e39adea0d990b2e315a
Source dataset
uspto-grants-2013_05
Patent number
US08450525B2

Reaction notes

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