Sodium Bicarbonate → HCID 68152353, compound

HRID 593357Notes

Reaction equation

HRID 593357 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][C:5]2[C:6](=O)[CH2:7][CH2:8][C:9]=2[CH:10]=1.[NH2:12][C:13]1[CH:14]=[CH:15][C:16]([F:27])=[C:17]([C@@:19]2([CH3:26])[NH:24][C:23](=[O:25])[CH2:22][O:21][CH2:20]2)[CH:18]=1.[B][B][B][B][B][B][B][B][B][B].C(=O)([O-])O.[Na+]>CO.ClCCl>[Cl:1][C:2]1[CH:3]=[N:4][C:5]2[CH:6]([NH:12][C:13]3[CH:14]=[CH:15][C:16]([F:27])=[C:17]([C@@:19]4([CH3:26])[NH:24][C:23](=[O:25])[CH2:22][O:21][CH2:20]4)[CH:18]=3)[CH2:7][CH2:8][C:9]=2[CH:10]=1

Participants

7

Reactant 4

HCID 516892Sodium BicarbonateHCID 58082858HCID 58082858, compoundHCID 58155273(R)-5-(5-amino-2-fluoro-phenyl)-5-methyl-morpholin-3-oneHCID 178419135HCID 178419135, compound

Product 1

HCID 68152353HCID 68152353, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 3-chloro-5,6-dihydro-[1]pyrindin-7-one (34.5 mg, 0.21 mmol) and (R)-5-(5-amino-2-fluoro-phenyl)-5-methyl-morpholin-3-one (50.1 mg, 0.22 mmol) in a mixture of methanol (7.3 ml) and dichloromethane (0.9 ml) was treated with decaborane (6.9 mg, 0.21 mmol). The reaction mixture was stirred at room temperature for 22 hours. For the workup, the mixture was poured into a saturated aqueous solution of sodium hydrogen carbonate, thereafter extracted with ethyl acetate. The combined organic layers were dried over sodium sulphate, then evaporated at reduced pressure. The crude material was purified by flash chromatography on silica gel using a gradient of heptane/ethyl acetate=100:0 to 20:80 as the eluent. The (R)-5-[5-((RS)-3-chloro-6,7-dihydro-5H-[1]pyrindin-7-ylamino)-2-fluoro-phenyl]-5-methyl-morpholin-3-one was obtained as an orange solid (50 mg, 71%); (calculated) C19H19ClFN3O2 [375.83]; (found) [M]+=376, [M+2]+=378.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe combined organic layers were dried over sodium sulphate
  3. customevaporated at reduced pressure
  4. customThe crude material was purified by flash chromatography on silica gel using a gradient of heptane/ethyl acetate=100:0 to 20:80 as the eluent

Sources & evidence

ORD record
ord-3d47638cfddb4a2f8b6143417c993357
Source dataset
uspto-grants-2016_01
Patent number
US09242943B2

Reaction notes

Loading…