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

HRID 469439Notes

Reaction equation

HRID 469439 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)[N:31]([CH3:36])[CH2:30][C:29]3([CH3:38])[CH3:37])=[O:25])[CH:19]=1.CCN(C(C)C)C(C)C>CN(C=O)C>[CH3:36][N:31]1[C:32]2[C:28](=[CH:27][C:26]([C:24]([C:20]3[N:21]=[CH:22][N:23]=[C:18]([N:1]4[CH2:2][CH2:3][CH:4]([N:7]5[C:15]6[C:10](=[N:11][CH:12]=[CH:13][CH:14]=6)[NH:9][C:8]5=[O:16])[CH2:5][CH2:6]4)[CH:19]=3)=[O:25])=[CH:34][C:33]=2[CH3:35])[C:29]([CH3:38])([CH3:37])[CH2:30]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 22293182Bms-973013HCID 58181090(6-chloro-pyrimidin-4-yl)-(1,3,3,7-tetramethyl-2,3-dihydro-1H-indol-5-yl)-methanone

Product 1

HCID 252676771-{1-[6-(1,3,3,7-tetramethyl-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

Conditions

Temperature
40 °C

Procedure

38 mg (0.17 mmol) 1-piperidin-4-yl-1,3-dihydroimidazo[4,5-b]pyridin-2-one, 55 mg (0.17 mmol) (6-chloro-pyrimidin-4-yl)-(1,3,3,7-tetramethyl-2,3-dihydro-1H-indol-5-yl)-methanone and 0.050 mL (0.29 mmol) DIPEA were combined in 2 mL DMF and stirred overnight at 40° C. Then the reaction mixture was purified by preparative HPLC-MS. The fractions containing the product were combined and freeze-dried.

Workup

  1. customThen the reaction mixture was purified by preparative HPLC-MS
  2. additionThe fractions containing the product
  3. customfreeze-dried

Sources & evidence

ORD record
ord-51994a4e5cb3446ca2dc50af40c5e730
Source dataset
uspto-grants-2014_01
Patent number
US08629137B2

Reaction notes

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