Propylamine → HCID 10515047, compound

HRID 2421638Notes

Reaction equation

HRID 2421638 reaction equation
CCN=C=[N:5][CH2:6][CH2:7][CH2:8]N(C)C.Cl.[C:13]1([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:18]=[CH:17][CH:16]=[C:15]([CH2:19][C:20]([OH:22])=O)[CH:14]=1.C(N)CC.C1C=CC2N(O)N=NC=2C=1>CC#N.CCOC(C)=O>[C:13]1([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:18]=[CH:17][CH:16]=[C:15]([CH2:19][C:20]([NH:5][CH2:6][CH2:7][CH3:8])=[O:22])[CH:14]=1

Participants

7

Reactant 4

HCID 7852PropylamineHCID 321533-Biphenylylacetic acidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 10515047HCID 10515047, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

EDAC.HCl (114 mg, 0.59 mmol) was added to a mixture of compound 91C (125 mg, 0.59 mmol), propylamine (49 μL, 0.59 mmol) and HOBT (80 mg, 0.59 mmol) in 1 mL of CH3CN. The reaction was stirred for 72 hours. After this time, the mixture was diluted with AcOEt. The organic layer was washed three times with HCl 2N, three times with NaOH 2N, dried over MgSO4 and concentrated. A with solid was obtained (100 mg, 67%). NMR 1H (ppm, CDCl3): 7.57 (d., J3=7.05 Hz, 2H), 7.52-7.32 (m, 6H), 7.23 J3=7.94 Hz, 1H), 5.65 (br. s., 1H), 3.62 (s, 2H), 3.20-3.13 (m, 2H), 1.44 (sex. J3=7.21 Hz, 2H), 0.83 (t, J3=7.43 Hz, 3H). NMR 13C (ppm, CDCl3): 170.9, 141.9, 140.5, 135.5, 129.3, 128.8, 128.2, 127.5, 127.0, 126.0, 43.8, 41.3, 22.7, 11.2. MS (+ESI): M+H+: 254.3.

Workup

  1. washThe organic layer was washed three times with HCl 2N, three times with NaOH 2N
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. customA with solid was obtained (100 mg, 67%)

Sources & evidence

ORD record
ord-38fb4a4e81a4447e8449ff9fbf920980
Source dataset
uspto-grants-2011_06
Patent number
US07956216B2

Reaction notes

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