Dimethylformamide → HCID 178513755, compound

HRID 2193478Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([NH:11][C:12]2[S:20][C:15]3[CH2:16][NH:17][CH2:18][CH2:19][C:14]=3[C:13]=2[C:21]([NH2:23])=[O:22])=[O:10])=[C:4]([F:24])[CH:3]=1.[CH:25]1[CH:26]=[CH:27][C:28]2[N:33](O)[N:32]=[N:31][C:29]=2[CH:30]=1.CCN=C=NCCCN(C)C.CN([CH:49]=[O:50])C>>[NH:31]1[C:29]2[CH:30]=[CH:25][C:26]([C:49]([N:17]3[CH2:18][CH2:19][C:14]4[C:13]([C:21]([NH2:23])=[O:22])=[C:12]([NH:11][C:9](=[O:10])[CH2:8][C:5]5[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][C:4]=5[F:24])[S:20][C:15]=4[CH2:16]3)=[O:50])=[CH:27][C:28]=2[N:33]=[N:32]1

Participants

Reactant 4

HCID 6228Dimethylformamide

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide

HCID 757711-Hydroxybenzotriazole

HCID 66662412HCID 66662412, compound

Product 1

HCID 178513755HCID 178513755, compoundYield 12%

Conditions

Temperature: 80 °C

Procedure

Starting material 20 (118 mg, 0.3 mmol) was suspended in 2 ml dry DMF and 1H-1,2,3-benzothiazole-5-carboxyllic acid (63 mg, 0.4 mmol, 1.2 equiv.), dry HOBt (52 mg, 0.4 mmol) and EDCI (74 mg, 0.4 mmol) were added. The brown suspension was stirred at 80° C. over night. Then another 0.5 equiv. 1H-1,2,3-benzothiazole-5-carboxyllic acid were added and the reaction was stirred another 6 h at 80° C. the solvent was reduced under vacuo and the remaining crude product further purified by prep. HPLC (Method 3). The pure fractions were combined and the solvent was reduced. The remaining product was lyophilized yielding the desired products 21 as a light-brown solid (20 mg, 0.04 mmol, 12%).

Workup

stirringthe reaction was stirred another 6 h at 80° C. the solvent
customthe remaining crude product further purified by prep

Sources & evidence

ORD record: ord-3b37a825ddd04af09606ccc6a7bfc2d2
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08329907B2

Reaction notes

Loading…