Dimethylformamide → HCID 178513755, compound

HRID 455010Notes

Reaction equation

HRID 455010 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.Cl.CN([CH:50]=[O:51])C>>[NH:31]1[C:29]2[CH:30]=[CH:25][C:26]([C:50]([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:51])=[CH:27][C:28]=2[N:33]=[N:32]1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 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 EDCl (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

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

Sources & evidence

ORD record
ord-f68787acac7c4b778935859d842405fd
Source dataset
uspto-grants-2013_07
Patent number
US08497283B2

Reaction notes

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