Acetic Acid → HCID 178478339, compound

HRID 1678770Notes

Reaction equation

HRID 1678770 reaction equation
[Cl:1][C:2]1[N:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[C:5]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:6]([C:12]1[CH:19]=[CH:18][C:15]([CH:16]=O)=[CH:14][CH:13]=1)=[N:7]2.[NH:26]1[CH2:31][CH2:30][CH:29]([C:32]2[N:36]=[C:35]([C:37]3[N:42]=[CH:41][CH:40]=[CH:39][N:38]=3)[NH:34][N:33]=2)[CH2:28][CH2:27]1.C(N(CC)CC)C.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CN1C(=O)CCC1.C(OCC)(=O)C>[Cl:1][C:2]1[N:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[C:5]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:6]([C:12]1[CH:19]=[CH:18][C:15]([CH2:16][N:26]3[CH2:27][CH2:28][CH:29]([C:32]4[NH:36][C:35]([C:37]5[N:42]=[CH:41][CH:40]=[CH:39][N:38]=5)=[N:34][N:33]=4)[CH2:30][CH2:31]3)=[CH:14][CH:13]=1)=[N:7]2

Participants

8

Reactant 5

HCID 176Acetic AcidHCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 575007324-(5-Chloro-3-phenyl-1,6-naphthyridin-2-yl)benzaldehydeHCID 178420762HCID 178420762, compound

Product 1

HCID 178478339HCID 178478339, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a stirred solution of 9-1 (0.25 g, 0.73 mMol) and 11-1 (0.23 g, 0.87 mMol) in NMP (5 mL) was added triethylamine (0.3 mL, 2.2 mMol) followed by acetic acid (0.082 mL, 1.5 mMol). After stirring at ambient temperature overnight, sodium triacetoxyborohydride (0.18 g, 0.87 mMol) was added. Upon completion, the reaction was diluted with ethyl acetate and washed with saturated NaHCO3, followed by water, then brine. The organic layer was dried with Na2SO4 and MgSO4, filtered and concentrated in vacuo to yield 11-2. LC/MS calculated: 559.1; observed: 559.3

Workup

  1. washwashed with saturated NaHCO3
  2. dry with materialThe organic layer was dried with Na2SO4 and MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto yield 11-2

Sources & evidence

ORD record
ord-38f04832392d44f58108f872ffe038aa
Source dataset
uspto-grants-2011_08
Patent number
US08008317B2

Reaction notes

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