Dimethylformamide → HCID 57813670, compound

HRID 447062Notes

Reaction equation

HRID 447062 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]([C:9]2[C:17]3[S:16][C:15]([NH:18][C:19]([NH:21][CH2:22][CH3:23])=[O:20])=[N:14][C:13]=3[CH:12]=[C:11](OS(C(F)(F)F)(=O)=O)[CH:10]=2)=[N:7][CH:8]=1)#[N:2].[N:32]1[CH:37]=[CH:36][CH:35]=[C:34](B(O)O)[CH:33]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CN(C)C=O>O>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([C:9]2[C:17]3[S:16][C:15]([NH:18][C:19]([NH:21][CH2:22][CH3:23])=[O:20])=[N:14][C:13]=3[CH:12]=[C:11]([C:34]3[CH:33]=[N:32][CH:37]=[CH:36][CH:35]=3)[CH:10]=2)=[N:7][CH:8]=1)#[N:2]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 27343783-Pyridinylboronic acidHCID 57813596HCID 57813596, compound

Product 1

HCID 57813670HCID 57813670, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A stirred mixture of the crude trifluoro-methanesulfonic acid 7-(5-cyano-pyridin-2-yl)-2-(3-ethyl-ureido)-benzothiazol-5-yl ester (108 mg, 0.23 mmol), 3-pyridineboronic acid (56 mg, 0.46 mmol), aqueous caesium carbonate (0.155 ml, 0.57 mmol, 3.7M), dimethylformamide (2.4 ml) and water (0.4 ml) was purged with nitrogen for 15 min. treated with tetrakistriphenylphosphine palladium (0) (27 mg, 0.023 mmol), sealed and heated at 80° C. for 8 h. After cooling to ambient temperature, the mixture was filtered through celite and washed through with methanol. The filtrate was evaporated in vacuo to give the crude 1-[7-(5-Cyano-pyridin-2-yl)-5-pyridin-3-yl-benzothiazol-2-yl]-3-ethyl-urea as a brown solid.

Workup

  1. customwas purged with nitrogen for 15 min.
  2. customsealed
  3. temperatureAfter cooling to ambient temperature
  4. filtrationthe mixture was filtered through celite
  5. washwashed through with methanol
  6. customThe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-e11860cf0b2347f69c907a931f5116a5
Source dataset
uspto-grants-2013_07
Patent number
US08481544B2

Reaction notes

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