Sodium Bicarbonate → HCID 10369545, compound

HRID 1795460Notes

Reaction equation

HRID 1795460 reaction equation
[CH3:1][N:2]1[C:7]([CH:8]2[CH2:12][CH2:11][NH:10][CH2:9]2)=[CH:6][C:5]([C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)=[C:4]([C:19]2[CH:28]=[CH:27][C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH:20]=2)[C:3]1=[O:29].CN1C(=O)C(C2C=CC3C(=CC=CC=3)C=2)=C(C2C=CN=CC=2)C=C1C1CCNCC1.[C:60]([O:64][C:65](=[O:70])[NH:66][CH2:67][CH:68]=O)([CH3:63])([CH3:62])[CH3:61].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])(O)=O.[Na+]>C(Cl)(Cl)Cl.C(Cl)Cl>[C:60]([O:64][C:65](=[O:70])[NH:66][CH2:67][CH2:68][N:10]1[CH2:11][CH2:12][CH:8]([C:7]2[N:2]([CH3:1])[C:3](=[O:29])[C:4]([C:19]3[CH:28]=[CH:27][C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[CH:20]=3)=[C:5]([C:13]3[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=3)[CH:6]=2)[CH2:9]1)([CH3:63])([CH3:62])[CH3:61]

Participants

8

Reactant 5

HCID 516892Sodium BicarbonateHCID 4247255tert-butyl N-(2-oxoethyl)carbamateHCID 5049666Sodium triacetoxyborohydrideHCID 22185184HCID 22185184, compoundHCID 69588867HCID 69588867, compound

Product 1

HCID 10369545HCID 10369545, compoundYield 18%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 1-methyl-3-naphthalen-2-yl-6-pyrrolidin-3-yl-1H-[4,4′]bipyridinyl-2-one (prepared following the same method as described for 1′-methyl-5′-naphthalen-2-yl-1,2,3,4,5,6-hexahydro-1′H-[4,2′;4′,4″]terpyridin-6′-one, Scheme 12) (200 mg, 0.52 mmol) in dry CHCl3 (5 mL) under nitrogen was added (2-oxo-ethyl)-carbamic acid tert-butyl ester (209 mg, 1.3 mmol) and sodium triacetoxy borohydride (165 mg, 0.78 mmol) and then heated at 80° C. for 2 h. After cooling down to RT the mixture was diluted with CH2Cl2 and sat solution of NaHCO3 and the organic layer was taken. The organic phase was successively washed with H2O, brine and dried (Na2SO4). The crude was purified by flash chromatography (3%, 2M methanol ammonia in DCM) to obtain the title compound (50 mg, 18%) as a yellow solid. MS (ES+): 525 (M+H)+.

Workup

  1. temperatureAfter cooling down to RT the mixture
  2. washThe organic phase was successively washed with H2O, brine
  3. dry with materialdried (Na2SO4)
  4. customThe crude was purified by flash chromatography (3%, 2M methanol ammonia in DCM)

Sources & evidence

ORD record
ord-deeb8818156e49f098186260897ddb4f
Source dataset
uspto-grants-2006_04
Patent number
US07026326B2

Reaction notes

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