4-Methylmorpholine → HCID 178485332, compound

HRID 1270826Notes

Reaction equation

HRID 1270826 reaction equation
[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16]([NH:18][CH:19]([C:30](=[O:48])[N:31]3[CH2:36][CH2:35][CH2:34][CH2:33][CH:32]3C3NC=C(C4C=CC=CC=4)N=3)[CH2:20][C:21]3[CH:29]=[CH:28][C:24]([C:25]([OH:27])=O)=[CH:23][CH:22]=3)=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.Cl.CN.C[N:53]1[CH2:58]COCC1.O.ON1[C:65]2[CH:66]=CC=[CH:69][C:64]=2N=N1.Cl.CN(C)[CH2:73][CH2:74][CH2:75][N:76]=[C:77]=[N:78][CH2:79]C>CN(C)C=O>[CH:10]1[C:11]2[CH:12]([CH2:14][O:15][C:16](=[O:17])[NH:18][CH:19]([CH2:20][C:21]3[CH:22]=[CH:23][C:24]([C:25](=[O:27])[NH:53][CH3:58])=[CH:28][CH:29]=3)[C:30](=[O:48])[N:31]3[CH2:36][CH2:35][CH2:34][CH2:33][CH:32]3[C:77]3[NH:78][CH:79]=[C:75]([C:74]4[CH:73]=[CH:66][CH:65]=[CH:64][CH:69]=4)[N:76]=3)[C:13]3[C:5](=[CH:4][CH:3]=[CH:2][CH:1]=3)[C:6]=2[CH:7]=[CH:8][CH:9]=1

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 6364545Methylamine hydrochlorideHCID 178523214HCID 178523214, compound

Product 1

HCID 178485332HCID 178485332, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 150 mg (0.23 mmol) of the product from step B, 17 mg (0.25 mmol) of methylamine hydrochloride, 27 uL (0.25 mmol) of N-methylmorpholine, 62 mg (0.46 mmol) of 1-hydroxybenzotriazole hydrate, and 57 mg (0.3 mmol) of of 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride was added 2 mL of dimethylformamide. The resulting mixture was allowed to stir at room temperature under argon for 5.5 hours. The mixture was partitioned between ethyl acetate and water and separated. The organic layer was dried over MgSO4 and concentrated. Obtained 148 mg (0.21 mmol, 92% yield) of crude product.

Workup

  1. customThe mixture was partitioned between ethyl acetate and water
  2. customseparated
  3. dry with materialThe organic layer was dried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-ebb0a66e162c4f6589528550bbb62a31
Source dataset
uspto-grants-2007_04
Patent number
US07202381B2

Reaction notes

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