Dimethylformamide → HCID 68772556, compound

HRID 2098570Notes

Reaction equation

HRID 2098570 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.[NH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][C:48]([O:50][CH3:51])=[O:49].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:42][CH2:43][CH2:44][CH2:45][CH:46]=[CH:47][C:48]([O:50][CH3:51])=[O:49])=[O:19])=[CH:12][CH:11]=2)[CH2:25][CH2:26]1

Participants

7

Reactant 5

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 1810164Methyl 6-aminohexanoateHCID 68424066HCID 68424066, compound

Product 1

HCID 68772556HCID 68772556, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a suspension of 3-(1E)-(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-I) (0.35 g, 1 mmol) in DMF (15 mL) EDCI (0.83 g, 2 mmol), HOBt (0.13 g, 1 mmol), methyl 6-aminocaproate (0.16 g, 0.9 mmol), were added, followed by triethylamine (0.4 mL, 3 mmol). The reaction mixture was stirred for 2 hours after which the mixture was added to cold water (50 mL). The aqueous layer was extracted with ethyl organic layer was dried over anhydrous Na2SO4 and concentrated to get the crude compound. The crude yellow colored compound was washed with ethyl acetate/hexane (0.5/9.5, 2×20 mL) to afford the title compound as a yellow solid (0.25 g, 52% yield).

Workup

  1. customprepared
  2. extractionThe aqueous layer was extracted with ethyl organic layer
  3. dry with materialwas dried over anhydrous Na2SO4
  4. concentrationconcentrated
  5. customto get the crude compound
  6. washThe crude yellow colored compound was washed with ethyl acetate/hexane (0.5/9.5, 2×20 mL)

Sources & evidence

ORD record
ord-fc79db691d0c476bbbd8dc50de5dc3a6
Source dataset
uspto-grants-2013_05
Patent number
US08450525B2

Reaction notes

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