Diisopropylethylamine → HCID 68194764, compound

HRID 2370654Notes

Reaction equation

HRID 2370654 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[N:9]1[C:14](=[O:15])[C:13]2[CH:16]=[N:17][C:18]([NH:20][C:21]3[CH:29]=[CH:28][C:24]([C:25](O)=[O:26])=[CH:23][CH:22]=3)=[N:19][C:12]=2[N:11]2[CH:30]=[CH:31][N:32]=[C:10]12.Cl.C(N=C=NCCCN(C)C)C.O.ON1C2C=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C.[CH3:65][N:66]([CH3:73])[CH:67]1[CH2:72][CH2:71][NH:70][CH2:69][CH2:68]1>CN(C)C=O.C(OCC)(=O)C>[Cl:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=1[N:9]1[C:14](=[O:15])[C:13]2[CH:16]=[N:17][C:18]([NH:20][C:21]3[CH:22]=[CH:23][C:24]([C:25]([N:70]4[CH2:71][CH2:72][CH:67]([N:66]([CH3:73])[CH3:65])[CH2:68][CH2:69]4)=[O:26])=[CH:28][CH:29]=3)=[N:19][C:12]=2[N:11]2[CH:30]=[CH:31][N:32]=[C:10]12

Participants

8

Reactant 5

HCID 81531DiisopropylethylamineHCID 417391N,N-Dimethylpiperidin-4-amineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 68195236HCID 68195236, compound

Product 1

HCID 68194764HCID 68194764, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of Example 237A (100 mg, 0.214 mmol) in 5 mL N,N-dimethylformamide was added 1-ethyl-3-[3-(dimethylamino)propyl]-carbodiimide hydrochloride (61.5 mg, 0.321 mmol), 1-hydroxybenzotriazole hydrate (49.2 mg, 0.321 mmol), diisopropylethylamine (0.075 ml, 0.428 mmol) followed by N,N-dimethylpiperidin-4-amine (0.036 ml, 0.257 mmol). The reaction mixture was held at room temperature overnight, and then diluted with ethyl acetate. The organics were washed with aqueous saturated NaHCO3, water, and brine, then dried over MgSO4, filtered, and concentrated. The compound was triturated from the crude reaction mixture to provide the title compound. 1H NMR (300 MHz, DMSO-d6) δ 1.21-1.55 (m, 2H) 1.63-1.98 (m, 2H) 2.13-2.43 (m, 6H) 2.73-3.12 (m, 2H) 7.14 (d, J=1.59 Hz, 1H) 7.48 (d, J=8.73 Hz, 2H) 7.58-7.81 (m, 4H) 7.86-8.02 (m, 3H) 9.06-9.33 (m, 1H) 11.04 (s, 1H). MS (ESI+) m/z 477.1 (M+H)+.

Workup

  1. washThe organics were washed with aqueous saturated NaHCO3, water, and brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe compound was triturated from the crude
  6. customreaction mixture

Sources & evidence

ORD record
ord-319139e82f4b493ab5cc6b671ac3cf3f
Source dataset
uspto-grants-2014_04
Patent number
US08710065B2

Reaction notes

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