Triethylamine → 2-Amino-N-(6-benzyloxy-benzofuran-2-ylmethyl)-6-methoxymethyl-nicotinamide

HRID 1171191Notes

Reaction equation

HRID 1171191 reaction equation
[CH2:1]([O:8][C:9]1[CH:19]=[CH:18][C:12]2[CH:13]=[C:14]([CH2:16][NH2:17])[O:15][C:11]=2[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:20][C:21]1[N:29]=[C:28]([CH2:30][O:31][CH3:32])[CH:27]=[CH:26][C:22]=1[C:23](O)=[O:24].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>O.CN(C)C=O>[NH2:20][C:21]1[N:29]=[C:28]([CH2:30][O:31][CH3:32])[CH:27]=[CH:26][C:22]=1[C:23]([NH:17][CH2:16][C:14]1[O:15][C:11]2[CH:10]=[C:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH:19]=[CH:18][C:12]=2[CH:13]=1)=[O:24]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 231304372-Amino-6-methoxymethylnicotinic acidHCID 57608217C-(6-Benzyloxybenzofuran-2-yl)-methylamine

Product 1

HCID 119607292-Amino-N-(6-benzyloxy-benzofuran-2-ylmethyl)-6-methoxymethyl-nicotinamideYield 69%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a N,N-dimethylformamide (8 mL) solution of C-(6-benzyloxy-benzofuran-2-yl)-methylamine (400 mg, 1.58 mmol) described in Production Example 1-2-4 were added 2-amino-6-methoxymethyl-nicotinic acid (316 mg, 1.74 mmol) described in Production Example 4-1-5, triethylamine (660 μL, 4.74 mmol) and benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (908 mg, 2.05 mmol) at room temperature, which was stirred at room temperature for 2 hours 30 minutes. To the reaction solution was added water at room temperature followed by extraction with ethyl acetate. After washing the organic layer with water and sat. NaCl, the organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under a reduced pressure and purified by silica gel column chromatography (heptane:ethyl acetate=1:2) to obtain the title compound (454 mg, 69%) as a white solid.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washAfter washing the organic layer with water and sat. NaCl
  3. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under a reduced pressure
  6. custompurified by silica gel column chromatography (heptane:ethyl acetate=1:2)

Sources & evidence

ORD record
ord-6dff2aaa34574a90a224ea37a433b431
Source dataset
uspto-grants-2010_11
Patent number
US07829585B2

Reaction notes

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