Acetic Acid → HCID 117667718, compound

HRID 712745Notes

Reaction equation

HRID 712745 reaction equation
[C:1]([C:3]1[C:8]([C:9]2[CH:10]=[C:11]3[C:16](=[N:17][CH:18]=2)[N:15]([C:19]([NH2:21])=[O:20])[CH2:14][CH2:13][CH2:12]3)=[CH:7][N:6]=[CH:5][C:4]=1[CH:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1)#[N:2].[C:28](O)(=[O:30])[CH3:29].C(N(CC)CC)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>C(#N)C>[C:28]([N:25]1[CH2:26][CH2:27][CH:22]([C:4]2[CH:5]=[N:6][CH:7]=[C:8]([C:9]3[CH:10]=[C:11]4[C:16](=[N:17][CH:18]=3)[N:15]([C:19]([NH2:21])=[O:20])[CH2:14][CH2:13][CH2:12]4)[C:3]=2[C:1]#[N:2])[CH2:23][CH2:24]1)(=[O:30])[CH3:29]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8471TriethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 117667622HCID 117667622, compound

Product 1

HCID 117667718HCID 117667718, compoundYield 42.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The crude 6-(4-cyano-1′,2′,3′,4′,5′,6′-hexahydro-[3,4]bipyridinyl-5-yl)-3,4-dihydro-2H-[1,8]naphthyridine-1-carboxylic acid amide (0.22 mmol), acetic acid (0.025 mL, 0.43 mmol) and triethyl amine (0.091 mL, 0.65 mmol) are mixed in acetonitrile (2.5 mL). Then TBTU (104 mg, 0.33 mmol) is added and the mixture is stirred for 16 hrs. All the solvent is removed and the residue is purified by flash column chromatography to give 38 mg of the titled product.

Workup

  1. customAll the solvent is removed
  2. customthe residue is purified by flash column chromatography

Sources & evidence

ORD record
ord-59e74a6fd6d44e7e8ca6a301876f8b48
Source dataset
uspto-grants-2015_11
Patent number
US09181272B2

Reaction notes

Loading…