Water → HCID 68406708, compound

HRID 2098580Notes

Reaction equation

HRID 2098580 reaction equation
[CH:1]1([NH:4][CH2:5][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]([OH:14])=O)=[CH:10][CH:9]=2)[CH2:3][CH2:2]1.CCN=C=NCCCN(C)C.Cl.[CH:36]1[CH:37]=[CH:38][C:39]2[N:44](O)N=[N:42][C:40]=2[CH:41]=1.O>CN(C=O)C>[NH2:42][C:40]1[CH:41]=[CH:36][CH:37]=[CH:38][C:39]=1[NH:44][C:12](=[O:14])[C:11]1[CH:15]=[CH:16][C:8]([CH:7]=[C:6]([C:17]2[CH:18]=[CH:19][C:20]([F:23])=[CH:21][CH:22]=2)[CH2:5][NH:4][CH:1]2[CH2:2][CH2:3]2)=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 68769074HCID 68769074, compound

Product 1

HCID 68406708HCID 68406708, compoundYield 9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-(3-(cyclopropylamino)-2-(4-fluorophenyl)prop-1-en-1-yl)benzoic acid (0.4 g, 1.3 mmol) in DMF (5 mL), EDCl (0.49 g, 2.6 mmol), HOBt (0.175 g. 1.3 mmol) and TEA (0.54 mL, 3.9 mmol), were added, followed by n-phenylenediamine (0.280 g, 2.6 mmol). The reaction mixture was stirred at room temperature for 2 hours, subsequently the residue was poured into water and extracted with ethyl acetate (300 mL) and washed with water (3×50 mL) and brine (100 mL). The organic layer was dried over anhydrous Na2SO4 and concentrated to afford the crude compound. The obtained compound was purified with flash chromatography using 15% ethyl acetate/hexane as the eluent, pure fraction evaporated to afford title compound (0.040 g, 9% yield). 1H NMR (DMSO-d6) δ (ppm): 0.24-0.25 (2H, m, —CH2), 0.37-0.39 (2H, m, —CH2), 2.13-2.14 (1H, m, —CH), 3.57 (2H, s, —CH2), 4.86 (2H, s, —NH2), 6.55-6.59 (1H, t, Ar—H), 6.70 (1H, s, ═CH), 6.74-6.76 (1H, d, Ar—H), 6.93-6.95 (1H, t, Ar—H), 7.02-7.04 (2H, m, Ar—H), 7.10-7.12 (1H, d, Ar—H), 7.16-7.26 (4H, m, Ar—H), 7.74-7.76 (2H, d, Ar—H), 9.52 (1H, s, —NH), MS m/z: 402.2 (M++1).

Workup

  1. extractionextracted with ethyl acetate (300 mL)
  2. washwashed with water (3×50 mL) and brine (100 mL)
  3. dry with materialThe organic layer was dried over anhydrous Na2SO4
  4. concentrationconcentrated
  5. customto afford the crude compound
  6. customThe obtained compound was purified with flash chromatography
  7. customevaporated

Sources & evidence

ORD record
ord-f6ca154dd0b14466ac83ed62077ccc57
Source dataset
uspto-grants-2013_05
Patent number
US08450525B2

Reaction notes

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