Acetic Acid → HCID 178481265, compound

HRID 1678776Notes

Reaction equation

HRID 1678776 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[N:19]3[C:10]([C:11]4[CH:12]=[C:13]([C:28]5[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=5)[C:14]([C:20]5[CH:27]=[CH:26][C:23]([CH:24]=O)=[CH:22][CH:21]=5)=[N:15][C:16]=4[CH:17]=[CH:18]3)=[N:9][N:8]=2)[N:4]=[CH:3]1.Cl.Cl.[NH:36]1[CH2:41][CH2:40][CH:39]([C:42]2[N:46]=[C:45]([C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][N:48]=3)[NH:44][N:43]=2)[CH2:38][CH2:37]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>[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[N:19]3[C:10]([C:11]4[CH:12]=[C:13]([C:28]5[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=5)[C:14]([C:20]5[CH:27]=[CH:26][C:23]([CH2:24][N:36]6[CH2:41][CH2:40][CH:39]([C:42]7[NH:46][C:45]([C:47]8[CH:52]=[CH:51][CH:50]=[CH:49][N:48]=8)=[N:44][N:43]=7)[CH2:38][CH2:37]6)=[CH:22][CH:21]=5)=[N:15][C:16]=4[CH:17]=[CH:18]3)=[N:9][N:8]=2)[N:4]=[CH:3]1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 594728924-[3-(1-methyl-1H-imidazol-4-yl)-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl]benzaldehydeHCID 1784785342-(5-Piperidin-4-yl-4h-1,2,4-triazol-3-yl)-pyridine dihydrochloride

Product 1

HCID 178481265HCID 178481265, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a stirred solution of 13-2 (0.5 g, 1.2 mMol) and 8-5 (0.34 g, 1.3 mMol) in NMP (10 mL) was added triethylamine (0.33 mL, 2.3 mMol) followed by acetic acid (0.13 mL, 2.3 mMol). After stirring overnight at room temperature, sodium triacetoxyborohydride (0.3 g, 1.3 mMol) was added in portions. After stirring for 6 hours, the solution was filtered through a syringe filter and purified on a C18 reverse phase HPLC to give 13-3 as a solid. Mass (M+1) calculated: 644.2993 observed: 644.2988

Workup

  1. stirringAfter stirring for 6 hours
  2. filtrationthe solution was filtered through a syringe
  3. filtrationfilter
  4. custompurified on a C18 reverse phase HPLC

Sources & evidence

ORD record
ord-feda09550a7e4fe69e5c1e3a4b30dd44
Source dataset
uspto-grants-2011_08
Patent number
US08008317B2

Reaction notes

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