Dimethylformamide → HCID 178513757, compound
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:23])[NH:10][C:11]2[S:19][C:14]3[CH2:15][NH:16][CH2:17][CH2:18][C:13]=3[C:12]=2[C:20]([NH2:22])=[O:21])=[CH:4][CH:3]=1.[CH:24]1[CH:25]=[CH:26][C:27]2[N:32](O)[N:31]=[N:30][C:28]=2[CH:29]=1.CCN=C=NCCCN(C)C.CN([CH:48]=[O:49])C>>[NH:30]1[C:28]2[CH:29]=[CH:24][C:25]([C:48]([N:16]3[CH2:17][CH2:18][C:13]4[C:12]([C:20]([NH2:22])=[O:21])=[C:11]([NH:10][C:9]([NH:8][C:5]5[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=5)=[O:23])[S:19][C:14]=4[CH2:15]3)=[O:49])=[CH:26][C:27]=2[N:32]=[N:31]1Participants
Procedure
Starting material 5 (847 mg, 2.4 mmol) was suspended in DMF (8 ml) and 1H-1,2,3-benzothiazole-5-carboxyllic acid (473 mg, 2.9 mmol), dry HOBt (427 mg, 2.9 mmol) and EDCI (606 mg, 2.9 mmol) were added. The brown suspension was stirred at ambient temperature over the weekend. As the reaction was not complete yet, the reaction was further stirred at 80° for 4 h. Thereby a brown solution was formed. The solvent was evaporated in vacuo and the crude product was further purified by prep. HPLC (Method 1). The product fractions were merged, the solvent was evaporated and the product lyophilized. Thereby 310 mg of the desired product 6 (0.635 mmol, 28%) were isolated as a light brown solid and additional 58 mg of the same product with 76% content which could have been purified further.
Workup
- stirringthe reaction was further stirred at 80° for 4 h
- customThereby a brown solution was formed
- customThe solvent was evaporated in vacuo
- customthe crude product was further purified by prep
- customthe solvent was evaporated
Sources & evidence
- ORD record
- ord-2a5d1ef3b8bc4eddb30e2582f8aa7e0c
- Source dataset
- uspto-grants-2012_12
- Patent number
- US08329907B2
Reaction notes
Loading…