Diisopropylethylamine → 1-{1-[6-(7-Methyl-2,3-dihydro-benzofuran-5-carbonyl)-pyrimidin-4-yl]-piperidin-4-yl}-1,3-di-hydro-imidazo[4,5-b]pyridin-2-one formate

HRID 469433Notes

Reaction equation

HRID 469433 reaction equation
Cl.Cl.[NH:3]1[CH2:8][CH2:7][CH:6]([N:9]2[C:17]3[C:12](=[N:13][CH:14]=[CH:15][CH:16]=3)[NH:11][C:10]2=[O:18])[CH2:5][CH2:4]1.Cl[C:20]1[N:25]=[CH:24][N:23]=[C:22]([C:26]([C:28]2[CH:29]=[C:30]([CH3:37])[C:31]3[O:35][CH2:34][CH2:33][C:32]=3[CH:36]=2)=[O:27])[CH:21]=1.CCN(C(C)C)C(C)C>CN(C=O)C.Cl>[CH3:37][C:30]1[C:31]2[O:35][CH2:34][CH2:33][C:32]=2[CH:36]=[C:28]([C:26]([C:22]2[N:23]=[CH:24][N:25]=[C:20]([N:3]3[CH2:4][CH2:5][CH:6]([N:9]4[C:17]5[C:12](=[N:13][CH:14]=[CH:15][CH:16]=5)[NH:11][C:10]4=[O:18])[CH2:7][CH2:8]3)[CH:21]=2)=[O:27])[CH:29]=1.[CH:10]([O-:18])=[O:27]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 222931811-(piperidin-4-yl)-1H,2H,3H-imidazo[4,5-b]pyridin-2-one dihydrochlorideHCID 58181093(6-Chloro-pyrimidin-4-yl)-(7-methyl-2,3-dihydro-benzofuran-5-yl)-methanone

Product 1

HCID 1317311301-{1-[6-(7-Methyl-2,3-dihydro-benzofuran-5-carbonyl)-pyrimidin-4-yl]-piperidin-4-yl}-1,3-di-hydro-imidazo[4,5-b]pyridin-2-one formate

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 6228DimethylformamideSolvent

Procedure

0.11 g (0.36 mmol) 1-piperidin-4-yl-1,3-dihydroimidazo[4,5-b]pyridin-2-one-dihydrochloride, 90 mg (0.23 mmol) (6-chloro-pyrimidin-4-yl)-(7-methyl-2,3-dihydro-benzofuran-5-yl)-methanone and 0.20 mL (1.16 mmol) DIPEA were combined in 1.5 mL DMF and stirred for 48 h at RT. Then the reaction mixture was mixed with a few drops of hydrochloric acid 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-4b53e7e31c68437ca7f8b0802c09e689
Source dataset
uspto-grants-2014_01
Patent number
US08629137B2

Reaction notes

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