Acetic Acid → HCID 86305806, compound

HRID 712616Notes

Reaction equation

HRID 712616 reaction equation
[NH2:1][CH2:2][C:3]1[CH:4]=[C:5]([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:6]=[N:7][CH:8]=1.[C:22](O)(=[O:24])[CH3:23].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:22]([NH:1][CH2:2][C:3]1[CH:4]=[C:5]([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:6]=[N:7][CH:8]=1)(=[O:24])[CH3:23]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8471TriethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 117667425HCID 117667425, compound

Product 1

HCID 86305806HCID 86305806, compoundYield 89.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

6-(5-Aminomethyl-pyridin-3-yl)-3,4-dihydro-2H-[1,8]naphthyridine-1-carboxylic acid amide (38 mg, 0.13 mmol), acetic acid (0.015 mL, 0.27 mmol) and triethyl amine (0.056 mL, 0.40 mmol) are mixed in 2.5 mL of acetonitrile. Then TBTU (52 mg, 0.16 mmol) is added and the mixture is stirred for 1 hrs. All the solvents are removed and the residue is first purified by flash column chromatography and then filtered through a StratoSpheres SPE cartridge (PL-HCO3 MP SPE) to remove the HOBt. The filtrate is concentrated and dried to give 38 mg of the titled product.

Workup

  1. customAll the solvents are removed
  2. customthe residue is first purified by flash column chromatography
  3. filtrationfiltered through a StratoSpheres SPE cartridge (PL-HCO3 MP SPE)
  4. customto remove the HOBt
  5. concentrationThe filtrate is concentrated
  6. customdried

Sources & evidence

ORD record
ord-c0a51f6dab9a4b649ae141fefbc25f53
Source dataset
uspto-grants-2015_11
Patent number
US09181272B2

Reaction notes

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