Triethylamine → 2-Amino-N-(5-benzyloxy-benzofuran-2-ylmethyl)-6-methoxymethyl-nicotinamide

HRID 1171199Notes

Reaction equation

HRID 1171199 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]2[O:16][C:15]([CH2:17][NH2:18])=[CH:14][C:13]=2[CH:19]=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:18][CH2:17][C:15]1[O:16][C:12]2[CH:11]=[CH:10][C:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[CH:19][C:13]=2[CH:14]=1)=[O:24]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 231304372-Amino-6-methoxymethylnicotinic acidHCID 57608280C-(5-benzyloxy-benzofuran-2-yl)-methylamine

Product 1

HCID 119608302-Amino-N-(5-benzyloxy-benzofuran-2-ylmethyl)-6-methoxymethyl-nicotinamideYield 75%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a N,N-dimethylformamide (5 mL) solution of C-(5-benzyloxy-benzofuran-2-yl)-methylamine (135 mg, 533 μmol) described in Production Example 7-1-6 were added 2-amino-6-methoxymethyl-nicotinic acid (107 mg, 586 μmol) described in Production Example 4-1-5, triethylamine (223 μL, 1.60 mmol) and benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (306 mg, 693 μmol) at room temperature, which was stirred at room temperature for 27 hours. Water was added to the reaction solution at room temperature followed by extracting with ethyl acetate. The organic layer was washed with water and sat. NaCl followed by drying over anhydrous magnesium sulfate and filtering. The filtrate was concentrated under a reduced pressure and the residue was purified by silica gel column chromatography (heptane:ethyl acetate=1:5) to obtain the title compound (166 mg, 75%) as a white solid.

Workup

  1. extractionby extracting with ethyl acetate
  2. washThe organic layer was washed with water and sat. NaCl
  3. dry with materialby drying over anhydrous magnesium sulfate
  4. filtrationfiltering
  5. concentrationThe filtrate was concentrated under a reduced pressure
  6. customthe residue was purified by silica gel column chromatography (heptane:ethyl acetate=1:5)

Sources & evidence

ORD record
ord-54e6b7117f024c52b27b017922413678
Source dataset
uspto-grants-2010_11
Patent number
US07829585B2

Reaction notes

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