Sodium Hydroxide → HCID 131725722, compound

HRID 1822749Notes

Reaction equation

HRID 1822749 reaction equation
[C:1]1([C:7]2[N:12]=[C:11]3[CH:13]=[CH:14][N:15]=[CH:16][C:10]3=[C:9]([C:17]([OH:19])=O)[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.F[P-](F)(F)(F)(F)F.[N:27]1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C1([C@@H](N)CC)C=CC=CC=1.[OH-].[Na+]>CC(N(C)C)=O.ClC(Cl)C.C(N(CC)CC)C>[C:1]1([C:7]2[N:12]=[C:11]3[CH:13]=[CH:14][N:15]=[CH:16][C:10]3=[C:9]([C:17]([NH2:27])=[O:19])[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 6993773(1S)-1-phenylpropan-1-amineHCID 106821072-Phenyl-[1,6]naphthyridine-4-carboxylic acid

Product 1

HCID 131725722HCID 131725722, compound

Reagents, catalysts & solvents 3

HCID 63651,1-DichloroethaneSolventHCID 8471TriethylamineSolventHCID 31374DimethylacetamideSolvent

Procedure

To a solution of 250 mg of 2-phenylpyridino[4,3-b]pyridin-4-yl carboxylic acid dissolved in 5 mL of dimethylacetamide and 200 uL of triethylamine is added 500 mg of BOP in 5 mL of dichloroethane followed by 150 mg of (S)-1-phenylpropylamine. The reaction mixture is stirred for 16 hours at room temperature. The reaction mixture is poured onto 50 mL of 1N NaOH and the product is extracted with 25 mL of ethyl acetate. After drying over magnesium sulfate the solvent is removed in vacuo to afford N—[(S)-1-phenyl-1-propyl)]-(2-phenylpyridino[4,3-b]pyridin-4-yl)carboxamide as a solid.

Workup

  1. extractionthe product is extracted with 25 mL of ethyl acetate
  2. dry with materialAfter drying over magnesium sulfate the solvent
  3. customis removed in vacuo

Sources & evidence

ORD record
ord-9f9a46d99877422791292d7e71a718a4
Source dataset
uspto-grants-2006_05
Patent number
US07037922B1

Reaction notes

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