Picolinoyl Chloride Hydrochloride → Ethyl 1-(5-(2-(3-ethylureido)-7-(picolinamido)benzo[d]thiazol-5-yl)pyrimidin-2-yl)-4-methylpiperidine-4-carboxylate

HRID 712309Notes

Reaction equation

HRID 712309 reaction equation
[NH2:1][C:2]1[C:10]2[S:9][C:8]([NH:11][C:12]([NH:14][CH2:15][CH3:16])=[O:13])=[N:7][C:6]=2[CH:5]=[C:4]([C:17]2[CH:18]=[N:19][C:20]([N:23]3[CH2:28][CH2:27][C:26]([CH3:34])([C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH2:25][CH2:24]3)=[N:21][CH:22]=2)[CH:3]=1.Cl.[N:36]1[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=1[C:42](Cl)=[O:43]>N1C=CC=CC=1>[CH2:15]([NH:14][C:12](=[O:13])[NH:11][C:8]1[S:9][C:10]2[C:2]([NH:1][C:42](=[O:43])[C:37]3[CH:38]=[CH:39][CH:40]=[CH:41][N:36]=3)=[CH:3][C:4]([C:17]3[CH:18]=[N:19][C:20]([N:23]4[CH2:24][CH2:25][C:26]([CH3:34])([C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH2:27][CH2:28]4)=[N:21][CH:22]=3)=[CH:5][C:6]=2[N:7]=1)[CH3:16]

Participants

4

Reactant 2

HCID 135033Picolinoyl Chloride HydrochlorideHCID 86664019Ethyl 1-(5-(7-amino-2-(3-ethylureido)benzo[d]thiazol-5-yl)pyrimidin-2-yl)-4-methylpiperidine-4-carboxylate

Product 1

HCID 86664022Ethyl 1-(5-(2-(3-ethylureido)-7-(picolinamido)benzo[d]thiazol-5-yl)pyrimidin-2-yl)-4-methylpiperidine-4-carboxylateYield 68%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Ethyl 1-(5-(7-amino-2-(3-ethylureido)benzo[d]thiazol-5-yl)pyrimidin-2-yl)-4-methylpiperidine-4-carboxylate (119 mg, 0.25 mmol) was dissolved in pyridine (2 ml) then picolinoyl chloride hydrochloride (58 mg, 0.33 mmol) was added with stirring and the reaction stirred at rt for 18 h. The pyridine was removed under reduced pressure and the residue triturated with water. The resulting solid was collected by filtration and dried to afford the crude product 100 mg (68%). This material was used directly in the next step without further purification.

Workup

  1. stirringthe reaction stirred at rt for 18 h
  2. customThe pyridine was removed under reduced pressure
  3. customthe residue triturated with water
  4. filtrationThe resulting solid was collected by filtration
  5. customdried

Sources & evidence

ORD record
ord-277f3e01570845bfb258ebfe078f5730
Source dataset
uspto-grants-2015_11
Patent number
US09181234B2

Reaction notes

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