Triethylamine → 2-Amino-6-chloro-N-(4-benzyloxy-benzyl)-nicotinamide

HRID 2080177Notes

Reaction equation

HRID 2080177 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.C(N(CC)CC)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.[CH2:46]([O:53][C:54]1[CH:61]=[CH:60][C:57]([CH2:58][NH2:59])=[CH:56][CH:55]=1)[C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1.N1C2C(=NC=CC=2)C=C1>CN(C)C=O.[Cl-].[Na+].O>[NH2:1][C:2]1[N:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[C:4]([NH:59][CH2:58][C:57]1[CH:60]=[CH:61][C:54]([O:53][CH2:46][C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)=[CH:55][CH:56]=1)=[O:6]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 92264-AzaindoleHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 42928454-BenzyloxybenzylamineHCID 122639922-Amino-6-chloronicotinic acid

Product 1

HCID 231305612-Amino-6-chloro-N-(4-benzyloxy-benzyl)-nicotinamideYield 22%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

2-Amino-6chloro-nicotinic acid described in Preparation Example A-1 (220 mg, 1.4 mmol), triethylamine (0.47 mL, 3.37 mmol) and benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (764 mg, 1.73 mmol) were dissolved in N,N-dimethylformamide (3 mL), 4-benzyloxy-benzylamine described in Preparation Example 1 (399 mg, 1.87 mmol) was added thereto, followed by stirring at room temperature for 17 hours 30 minutes. After the reaction was completed, the reaction solution was poured into brine, which was then extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, then concentrated, the obtained residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:1), and the title compound (115 mg, 0.31 mmol, 22%) was obtained.

Workup

  1. additionwas added
  2. extractionwas then extracted with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customthe obtained residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:1)

Sources & evidence

ORD record
ord-f0f4f72338ac42b3bb3f4d0f7720b8f1
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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