Diisopropylethylamine → 1-{1-[6-(7-methyl-2-oxo-2,3-dihydro-1H-indol-5-carbonyl)-pyrimidin-4-yl]-piperidin-4-yl}-1,3-dihydro-imidazo[4,5-b]pyridin-2-one

HRID 469424Notes

Reaction equation

HRID 469424 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:27]=[C:28]3[C:32](=[C:33]([CH3:35])[CH:34]=2)[NH:31][C:30](=[O:36])[CH2:29]3)=[O:25])[CH:19]=1.CCN(C(C)C)C(C)C.C(#N)C.O>CN(C=O)C>[CH3:35][C:33]1[CH:34]=[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:27]=[C:28]2[C:32]=1[NH:31][C:30](=[O:36])[CH2:29]2

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 18373917Acetonitrile--water (1/1)HCID 22293182Bms-973013HCID 581811435-(6-Chloro-pyrimidine-4-carbonyl)-7-methyl-1,3-dihydro-indol-2-one

Product 1

HCID 252662711-{1-[6-(7-methyl-2-oxo-2,3-dihydro-1H-indol-5-carbonyl)-pyrimidin-4-yl]-piperidin-4-yl}-1,3-dihydro-imidazo[4,5-b]pyridin-2-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

91 mg (0.42 mmol) 1-piperidin-4-yl-1,3-dihydroimidazo[4,5-b]pyridin-2-one, 120 mg (0.42 mmol) 5-(6-chloro-pyrimidine-4-carbonyl)-7-methyl-1,3-dihydro-indol-2-one and 0.080 mL (0.46 mmol) DIPEA were combined in 2 mL DMF and shaken overnight at RT. Then the reaction mixture was in taken up acetonitrile/water and purified by preparative HPLC-MS. The fractions containing the product were combined and freeze-dried.

Workup

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

Sources & evidence

ORD record
ord-a3deff32b91d4d08a626003e1ec7b93b
Source dataset
uspto-grants-2014_01
Patent number
US08629137B2

Reaction notes

Loading…