Bms-973013 → 1-[6'-benzyloxy-4'-(3,4-dimethyl-2-oxo-2,3-dihydro-benzoxazole-6-carbonyl)-3,4,5,6-tetra-hydro-2H-[1,2']bipyridinyl-4-yl]-1,3-dihydro-imidazo[4,5-b]pyridin-2-one

HRID 469425Notes

Reaction equation

HRID 469425 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.[CH2:17]([O:24][C:25]1[CH:30]=[C:29]([C:31]([C:33]2[CH:43]=[C:42]([CH3:44])[C:36]3[N:37]([CH3:41])[C:38](=[O:40])[O:39][C:35]=3[CH:34]=2)=[O:32])[CH:28]=[C:27](Cl)[N:26]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CN1C(=O)CCC1>[CH2:17]([O:24][C:25]1[N:26]=[C:27]([N:1]2[CH2:2][CH2:3][CH:4]([N:7]3[C:15]4[C:10](=[N:11][CH:12]=[CH:13][CH:14]=4)[NH:9][C:8]3=[O:16])[CH2:5][CH2:6]2)[CH:28]=[C:29]([C:31]([C:33]2[CH:43]=[C:42]([CH3:44])[C:36]3[N:37]([CH3:41])[C:38](=[O:40])[O:39][C:35]=3[CH:34]=2)=[O:32])[CH:30]=1)[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 22293182Bms-973013HCID 581811066-(2-benzyloxy-6-chloro-pyridine-4-carbonyl)-3,4-dimethyl-3H-benzoxazol-2-one

Product 1

HCID 252666191-[6'-benzyloxy-4'-(3,4-dimethyl-2-oxo-2,3-dihydro-benzoxazole-6-carbonyl)-3,4,5,6-tetra-hydro-2H-[1,2']bipyridinyl-4-yl]-1,3-dihydro-imidazo[4,5-b]pyridin-2-one

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
120 °C

Procedure

785 mg (3.60 mmol) 1-piperidin-4-yl-1,3-dihydroimidazo[4,5-b]pyridin-2-one and 500 mg (1.22 mmol) 6-(2-benzyloxy-6-chloro-pyridine-4-carbonyl)-3,4-dimethyl-3H-benzoxazol-2-one (mixture) were combined in 5 mL NMP and stirred overnight at 120° C. The reaction mixture was purified by preparative HPLC. The fractions containing the product were combined and evaporated down. The residue was triturated with DIPE, suction filtered, washed with DIPE and dried.

Workup

  1. customThe reaction mixture was purified by preparative HPLC
  2. additionThe fractions containing the product
  3. customevaporated down
  4. customThe residue was triturated with DIPE, suction
  5. filtrationfiltered
  6. washwashed with DIPE
  7. customdried

Sources & evidence

ORD record
ord-797c9fcda1a74cc08aee4782e4fd8991
Source dataset
uspto-grants-2014_01
Patent number
US08629137B2

Reaction notes

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