Ammonia → HCID 178513635, compound

HRID 931264Notes

Reaction equation

HRID 931264 reaction equation
[N:1]1([C:6]([C@@H:8]2[CH2:13][CH2:12][CH2:11][N:10]([C:14]3[N:19]=[C:18]4[NH:20][C:21]([C:23]5[N:28]=[C:27]([C:29](OC)=[O:30])[CH:26]=[CH:25][CH:24]=5)=[N:22][C:17]4=[CH:16][CH:15]=3)[CH2:9]2)=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.[NH3:33].C[Al](C)C>C1(C)C=CC=CC=1.O1CCOCC1>[N:1]1([C:6]([C@@H:8]2[CH2:13][CH2:12][CH2:11][N:10]([C:14]3[N:19]=[C:18]4[NH:20][C:21]([C:23]5[N:28]=[C:27]([C:29]([NH2:33])=[O:30])[CH:26]=[CH:25][CH:24]=5)=[N:22][C:17]4=[CH:16][CH:15]=3)[CH2:9]2)=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 16682925TrimethylaluminumHCID 178497691HCID 178497691, compound

Product 1

HCID 178513635HCID 178513635, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To (R)-methyl 6-(5-(3-(pyrrolidine-1-carbonyl)piperidin-1-yl)-3H-imidazo[4,5-b]pyridin-2-yl)picolinate (200 mg, 0.460 mmol) in toluene (5 mL) were added sequentially a freshly prepared saturated solution of ammonia in dioxane (10 mL) at −20° C., and trimethylaluminum (0.099 g, 1.348 mmol). The reaction vessel was sealed and was heated at 100° C. for 16 h. The mixture was cooled to room temperature and was partitioned between ethyl acetate, and water. The organic layer was dried over sodium sulfate and concentrated under reduced pressure. The resulting residue was triturated twice with methanol:diethyl ether (1:10) to afford the title compound (40 mg). MS (ES+) (M+H) 420.2892; LCMS retention time 3.71 min (Method I1).

Workup

  1. customThe reaction vessel was sealed
  2. temperatureThe mixture was cooled to room temperature
  3. customwas partitioned between ethyl acetate, and water
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was triturated twice with methanol:diethyl ether (1:10)

Sources & evidence

ORD record
ord-8ba9cbf1a72940ca9b5f0b9a122c71e8
Source dataset
uspto-grants-2016_03
Patent number
US09296745B2

Reaction notes

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