Piperidine → HCID 117667721, compound

HRID 712738Notes

Reaction equation

HRID 712738 reaction equation
[C:1]([N:4]1[C:13]2[N:12]=[CH:11][C:10]([C:14]3[CH:15]=[C:16]([CH2:20][O:21][CH2:22][C:23]([OH:25])=O)[CH:17]=[N:18][CH:19]=3)=[CH:9][C:8]=2[CH2:7][CH2:6][CH2:5]1)(=[O:3])[NH2:2].CN(C(ON1N=N[C:36]2[CH:37]=[CH:38][CH:39]=[N:40][C:35]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.N1CCCCC1.CCN(C(C)C)C(C)C>CN(C=O)C>[O:25]=[C:23]([N:40]1[CH2:35][CH2:36][CH2:37][CH2:38][CH2:39]1)[CH2:22][O:21][CH2:20][C:16]1[CH:15]=[C:14]([C:10]2[CH:9]=[C:8]3[C:13](=[N:12][CH:11]=2)[N:4]([C:1]([NH2:2])=[O:3])[CH2:5][CH2:6][CH2:7]3)[CH:19]=[N:18][CH:17]=1

Participants

6

Reactant 4

HCID 8082PiperidineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 117667724HCID 117667724, compound

Product 1

HCID 117667721HCID 117667721, compoundYield 30.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of [5-(8-carbamoyl-5,6,7,8-tetrahydro-[1,8]naphthyridin-3-yl)-pyridin-3-ylmethoxy]-acetic acid (80 mg, 0.23 mmol) in DMF (3 mL) is added HATU (107 mg, 0.28 mmol) followed by piperidine (20 mg, 0.23 mmol) and DIEA (0.26 ml, 1.50 mmol). The resulting mixture is stirred at room temperature for 2 hrs. The reaction is concentrated and the remaining residue is purified via flash column chromatography to give the titled product (29 mg).

Workup

  1. concentrationThe reaction is concentrated
  2. customthe remaining residue is purified via flash column chromatography

Sources & evidence

ORD record
ord-78dd6b31ca7d47b0b08b9421c3250948
Source dataset
uspto-grants-2015_11
Patent number
US09181272B2

Reaction notes

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