Diisopropylethylamine → 1-{1-[6-(4-Methyl-2-oxo-2,3-dihydro-benzothiazole-6-carbonyl)-pyrimidin-4-yl]-piperidin-4-yl}-1,3-dihydro-imidazo[4,5-b]pyridin-2-one

HRID 469418Notes

Reaction equation

HRID 469418 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([N:7]2[C:15]3[C:10](=[N:11][CH:12]=[CH:13][CH:14]=3)[NH:9][C:8]2=[O:16])[CH2:3][CH2:2]1.Cl[C:18]1[N:23]=[CH:22][N:21]=[C:20]([C:24]([C:26]2[CH:35]=[C:34]([CH3:36])[C:29]3[NH:30][C:31](=[O:33])[S:32][C:28]=3[CH:27]=2)=[O:25])[CH:19]=1.CCN(C(C)C)C(C)C>CN(C=O)C.C(#N)C.O>[CH3:36][C:34]1[C:29]2[NH:30][C:31](=[O:33])[S:32][C:28]=2[CH:27]=[C:26]([C:24]([C:20]2[N:21]=[CH:22][N:23]=[C:18]([N:1]3[CH2:2][CH2:3][CH:4]([N:7]4[C:15]5[C:10](=[N:11][CH:12]=[CH:13][CH:14]=5)[NH:9][C:8]4=[O:16])[CH2:5][CH2:6]3)[CH:19]=2)=[O:25])[CH:35]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 22293182Bms-973013HCID 581811306-(6-chloro-pyrimidine-4-carbonyl)-4-methyl-3H-benzothiazol-2-one

Product 1

HCID 252714891-{1-[6-(4-Methyl-2-oxo-2,3-dihydro-benzothiazole-6-carbonyl)-pyrimidin-4-yl]-piperidin-4-yl}-1,3-dihydro-imidazo[4,5-b]pyridin-2-one

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

50 mg (0.23 mmol) 1-piperidin-4-yl-1,3-dihydroimidazo[4,5-b]pyridin-2-one, 70.6 mg (0.23 mmol) 6-(6-chloro-pyrimidine-4-carbonyl)-4-methyl-3H-benzothiazol-2-one and 0.05 mL (0.27 mmol) DIPEA were combined in 2 mL DMF and shaken overnight at RT. The reaction mixture was taken up in acetonitrile/water and purified by preparative HPLC. The fractions containing the product were combined and freeze-dried.

Workup

  1. custompurified by preparative HPLC
  2. additionThe fractions containing the product
  3. customfreeze-dried

Sources & evidence

ORD record
ord-04033ad282dd4f7591c81f2dff86e65a
Source dataset
uspto-grants-2014_01
Patent number
US08629137B2

Reaction notes

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