Ammonium Chloride → HCID 57745589, compound

HRID 1256657Notes

Reaction equation

HRID 1256657 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][O:8][C:9]([NH:11][CH2:12][C:13]2[CH:21]=[CH:20][C:16]([C:17](O)=[O:18])=[CH:15][CH:14]=2)=[O:10])[CH:2]=1.[Cl-].[NH4+].F[P-](F)(F)(F)(F)F.[N:31]1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.CCN(C(C)C)C(C)C>CN(C=O)C.O>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][O:8][C:9](=[O:10])[NH:11][CH2:12][C:13]2[CH:21]=[CH:20][C:16]([C:17]([NH2:31])=[O:18])=[CH:15][CH:14]=2)[CH:2]=1

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 98173384-((((Pyridin-3-ylmethoxy)carbonyl)amino)methyl)benzoic acid

Product 1

HCID 57745589HCID 57745589, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 4-({[(pyridin-3-ylmethoxy)carbonyl]amino}methyl)benzoic acid (1.0 g, 3.49 mmol), ammonium chloride (0.47 g, 8.73 mmol) and BOP (2.32 g, 5.24 mmol) in DMF (10 mL) was treated with DIEA (1.13 g. 8.73 mmol) and the resulting solution was stirred at ambient temperature for 16 hours. The reaction mixture was diluted with water (150 mL) and the resulting solids were filtered, washed with additional water and dried in vacuo to give pyridin-3-ylmethyl{[4-(aminocarbonyl)phenyl]methyl}carbamate as a white solid. MS: cal'd 286 (MH+), exp 286 (MH+).

Workup

  1. filtrationthe resulting solids were filtered
  2. washwashed with additional water
  3. customdried in vacuo

Sources & evidence

ORD record
ord-c2328748a79b47e7aaa6b6211fe6ad1f
Source dataset
uspto-grants-2013_06
Patent number
US08461189B2

Reaction notes

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