Triethylamine → HCID 117667558, compound

HRID 712770Notes

Reaction equation

HRID 712770 reaction equation
[CH:1]1([C:4]([OH:6])=O)[CH2:3][CH2:2]1.[NH2:7][CH2:8][C:9]1[CH:10]=[C:11]([C:15]2[CH:16]=[C:17]3[C:22](=[N:23][CH:24]=2)[N:21]([C:25]([NH2:27])=[O:26])[CH2:20][CH2:19][CH2:18]3)[CH:12]=[N:13][CH:14]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C>CN(C=O)C>[CH:1]1([C:4]([NH:7][CH2:8][C:9]2[CH:10]=[C:11]([C:15]3[CH:16]=[C:17]4[C:22](=[N:23][CH:24]=3)[N:21]([C:25]([NH2:27])=[O:26])[CH2:20][CH2:19][CH2:18]4)[CH:12]=[N:13][CH:14]=2)=[O:6])[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 15655Cyclopropanecarboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 117667425HCID 117667425, compound

Product 1

HCID 117667558HCID 117667558, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To the cyclopropanecarboxylic acid (16 mg, 0.18 mmol) is added a solution of 6-(5-aminomethyl-pyridin-3-yl)-3,4-dihydro-2H-[1,8]naphthyridine-1-carboxylic acid amide (40 mg, 0.14 mmol) in DMF (1 mL) followed by HATU (100 mg, 0.26 mmol) in DMF (1 mL) followed by triethylamine (51 mg, 0.50 mmol). The mixture is stirred overnight. The mixture is concentrated in vacuo, dissolved in 2 mL of DMF, filtered and purified by reverse phase HPLC to afford the titled product.

Workup

  1. concentrationThe mixture is concentrated in vacuo
  2. dissolutiondissolved in 2 mL of DMF
  3. filtrationfiltered
  4. custompurified by reverse phase HPLC

Sources & evidence

ORD record
ord-913145c432b4442e8f42ca15e590a203
Source dataset
uspto-grants-2015_11
Patent number
US09181272B2

Reaction notes

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