4-Methylmorpholine → HCID 178521729, compound

HRID 2193484Notes

Reaction equation

HRID 2193484 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:20]=[C:21]([Cl:23])[CH:22]=1)[CH2:5][O:6][C:7](=[O:19])[NH:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[CH2:15][NH:14][CH2:13][CH2:12]2.CN1CC[O:28][CH2:27]C1.CCN=C=NCCCN(C)C.[CH:42]1[CH:43]=[CH:44][C:45]2[N:50](O)[N:49]=[N:48][C:46]=2[CH:47]=1>CN(C=O)C.O>[Cl:23][C:21]1[CH:20]=[C:4]([CH:3]=[C:2]([Cl:1])[CH:22]=1)[CH2:5][O:6][C:7](=[O:19])[NH:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[CH2:15][N:14]([C:27]([C:42]1[CH:43]=[CH:44][C:45]3[NH:50][N:49]=[N:48][C:46]=3[CH:47]=1)=[O:28])[CH2:13][CH2:12]2

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 66662781HCID 66662781, compound

Product 1

HCID 178521729HCID 178521729, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Starting material 47 (46 mg, 0.1 mmol), 1H-1,2,3-benzothiazole-5-carboxyllic acid (22 mg, 0.1 mmol) and 4-methyl morpholin (40 μL, 0.4 mmol) were dissolved in 2 ml DMF. Then EDCI (38 mg, 0.2 mmol) and HOBt (26 mg, 0.2 mmol) were added and the mixture was stirred over night at ambient temperature. The reaction mixture was mixed with water and the resulting precipitate was filtered and dried in vacuo at 45° C. The desired product 48 could thereby be isolated as light brown solid (34 mg, 0.07 mmol, 52%).

Workup

  1. filtrationthe resulting precipitate was filtered
  2. customdried in vacuo at 45° C

Sources & evidence

ORD record
ord-1a6f30355159430386d359f4186ee3e7
Source dataset
uspto-grants-2012_12
Patent number
US08329907B2

Reaction notes

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