Triethylamine → Benzothiazole-6-carboxylic acid 4-(3-fluoro-benzyloxy)-benzylamide

HRID 2080252Notes

Reaction equation

HRID 2080252 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][CH:17]=1)[CH2:5][O:6][C:7]1[CH:14]=[CH:13][C:10]([CH2:11][NH2:12])=[CH:9][CH:8]=1.[S:18]1[C:22]2[CH:23]=[C:24]([C:27](O)=[O:28])[CH:25]=[CH:26][C:21]=2[N:20]=[CH:19]1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C(N(CC)CC)C>O1CCCC1.O.C(OCC)(=O)C>[F:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][CH:17]=1)[CH2:5][O:6][C:7]1[CH:14]=[CH:13][C:10]([CH2:11][NH:12][C:27]([C:24]2[CH:25]=[CH:26][C:21]3[N:20]=[CH:19][S:18][C:22]=3[CH:23]=2)=[O:28])=[CH:9][CH:8]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 601670Benzothiazole-6-carboxylic acidHCID 167723641-{4-[(3-Fluorobenzyl)oxy]phenyl}methanamine

Product 1

HCID 58388098Benzothiazole-6-carboxylic acid 4-(3-fluoro-benzyloxy)-benzylamideYield 68%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-(3-fluorobenzyloxy)-benzylamine described in Preparation Example 6 (129 mg, 0.558 mmol) and benzothiazole-6-carboxylic acid (100 mg, 0.558 mmol) in tetrahydrofuran (5 mL) were added benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (296 mg, 0.670 mmol) and triethylamine (93 μl, 0.670 mmol), and the solution was stirred overnight at room temperature. Ethyl acetate and water were added to the reaction solution, which was then partitioned, the organic layer was washed with water, and then, dried over anhydrous magnesium sulfate. The solvent was evaporated, the residue was purified by NH silica gel column chromatography (hexane:ethyl acetate), and the title compound (148 mg, 68%) was obtained as a white solid.

Workup

  1. customwas then partitioned
  2. washthe organic layer was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated
  5. customthe residue was purified by NH silica gel column chromatography (hexane:ethyl acetate)

Sources & evidence

ORD record
ord-f86398251a174d1195608148f4ad9134
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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