3-Aminopyridine → HCID 66635289, compound

HRID 2204762Notes

Reaction equation

HRID 2204762 reaction equation
[Cl:1][C:2]1[C:3]([C:19]([N:21]2[CH2:25][CH2:24][C:23]([F:27])([F:26])[CH2:22]2)=[O:20])=[CH:4][C:5]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:6]([CH:10]=1)[C:7](O)=[O:8].C(N(C(C)C)CC)(C)C.CN(C(ON1N=[N:52][C:47]2[CH:48]=[CH:49][CH:50]=[N:51][C:46]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.NC1C=NC=CC=1>CN(C)C=O>[Cl:1][C:2]1[C:3]([C:19]([N:21]2[CH2:25][CH2:24][C:23]([F:26])([F:27])[CH2:22]2)=[O:20])=[CH:4][C:5]([O:11][CH2:12][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[C:6]([CH:10]=1)[C:7]([NH:52][C:47]1[CH:46]=[N:51][CH:50]=[CH:49][CH:48]=1)=[O:8]

Participants

6

Reactant 4

HCID 100093-AminopyridineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 66611762HCID 66611762, compound

Product 1

HCID 66635289HCID 66635289, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-chloro-4-[(3,3-difluoro-1-pyrrolidinyl)carbonyl]-2-[(phenylmethyl)oxy]benzoic acid (may be prepared as described in Description 65; 90 mg, 0.23 mmol) in N,N-dimethylformamide (3 ml) was added diisopropylethylamine (0.08 ml, 0.46 mmol), HATU (156 mg, 0.41 mmol) and 3-aminopyridine (25.7 mg, 0.27 mmol). The solution was stirred for 18 hours. The solvent removed in vacuo to give a gum. Purification by MDAP gave the title compound as a white solid. 65 mg.

Workup

  1. customThe solvent removed in vacuo
  2. customto give a gum
  3. customPurification by MDAP

Sources & evidence

ORD record
ord-dd9eaf0c9cfd42739c7b7f667665a09c
Source dataset
uspto-grants-2016_06
Patent number
US09365551B2

Reaction notes

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