4-Methylmorpholine → HCID 178501297, compound

HRID 220153Notes

Reaction equation

HRID 220153 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:10])[C@@H:5]1[CH2:9][CH2:8][CH2:7][NH:6]1.[NH:11]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][C:19]([C@H:22]3[CH2:27][CH2:26][C@H:25]([CH2:28][C:29](O)=[O:30])[CH2:24][CH2:23]3)=[CH:18][CH:17]=2)=[N:12]1.Cl.C(N=C=NCCCN(C)C)C.O.ON1C2C=CC=CC=2N=N1.CN1CCOCC1>CN(C)C=O>[NH:11]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][C:19]([C@H:22]3[CH2:23][CH2:24][C@H:25]([CH2:28][C:29]([N:6]4[CH2:7][CH2:8][CH2:9][C@H:5]4[C:4]([O:3][CH3:2])=[O:10])=[O:30])[CH2:26][CH2:27]3)=[CH:18][CH:17]=2)=[N:12]1

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2733200methyl L-prolinate hydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 178525543HCID 178525543, compound

Product 1

HCID 178501297HCID 178501297, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

L-Proline methyl ester hydrochloride (0.03 g, 0.18 mmol) was added to a stirred solution of the product from Example 37C (0.05 g, 0.17 mmol), 1-ethyl-3-[3-(dimethylamino)propyl]-carbodiimide hydrochloride (0.042 g, 0.22 mmol), 1-hydroxybenzotriazole hydrate (0.03 g, 0.22 mmol) and N-methyl morpholine (0.1 mL, 0.87 mmol) in N,N-dimethylformamide (4 mL) at room temperature. The reaction was stirred at room temperature for 12 h and then quenched by addition of water. It was then extracted with ethyl acetate (3×25 mL), the organic extracts washed with water, brine, dried (MgSO4) and concentrated to afford the titled compound as a clear oil. 1H NMR (500 MHz, DMSO-d6) δ ppm 1.09-1.18 (m, 2 H), 1.40-1.51 (m, 2 H), 1.75-1.86 (m, 6 H), 1.88-1.94 (m, 2 H), 2.13-2.27 (m, 3 H), 2.40-2.49 (m, 1 H), 3.51-3.58 (m, 2 H), 3.61 (s, 3 H), 4.30 (dd, J=10, 5 Hz, 1 H), 6.64 (d, J=3 Hz, 1 H), 7.27 (d, J=10 Hz, 2 H), 7.66-7.72 (m, 3 H).

Workup

  1. customquenched by addition of water
  2. extractionIt was then extracted with ethyl acetate (3×25 mL)
  3. washthe organic extracts washed with water, brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-d01caaf226fd42bbb57d4920c43e9305
Source dataset
uspto-grants-2012_06
Patent number
US08202878B2

Reaction notes

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