Ammonium Chloride → HCID 44178124, compound

HRID 1716505Notes

Reaction equation

HRID 1716505 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH:8][C:9]2[N:14]=[C:13]([C:15]3[S:19][C:18]([N:20]4[CH2:25][CH2:24][CH:23]([C:26]([OH:28])=O)[CH2:22][CH2:21]4)=[N:17][CH:16]=3)[CH:12]=[CH:11][CH:10]=2)[CH:3]=1.F[P-](F)(F)(F)(F)F.[NH:36]1C2C=CC=C(O[P+](N3CCCC3)(N3CCCC3)N3CCCC3)C=2N=N1.C(N(C(C)C)CC)(C)C.[Cl-].[NH4+].C(=O)(O)[O-].[Na+]>CN(C)C=O>[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH:8][C:9]2[N:14]=[C:13]([C:15]3[S:19][C:18]([N:20]4[CH2:21][CH2:22][CH:23]([C:26]([NH2:36])=[O:28])[CH2:24][CH2:25]4)=[N:17][CH:16]=3)[CH:12]=[CH:11][CH:10]=2)[CH:3]=1

Participants

7

Reactant 5

HCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 11560292HCID 11560292, compoundHCID 178506432HCID 178506432, compound

Product 1

HCID 44178124HCID 44178124, compoundYield 90.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-{5-[6-(4-methylpyridin-2-ylamino)pyridin-2-yl]thiazol-2-yl} piperidine-4-carboxylic acid (100 mg, 0.25 mmol) obtained in Example 2 was dissolved in N,N-dimethylformamide (2 ml) and benzotriazolyloxy trispyrrolidino phosphonium hexafluorophosphate (263 mg, 0.50 mmol), diisopropylethylamine (0.18 ml, 1.03 mmol) and ammonium chloride (41 mg, 0.77 mmol) were added and the mixture was stirred at room temperature for 1 hour. A saturated aqueous sodium bicarbonate was added to the reaction solution and the precipitated solid was collected by filtration and washed with water and title compound (89 mg, 89%) was obtained.

Workup

  1. filtrationthe precipitated solid was collected by filtration
  2. washwashed with water

Sources & evidence

ORD record
ord-79798ba0a9a948eea821514351debe4e
Source dataset
uspto-grants-2010_09
Patent number
US07803801B2

Reaction notes

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