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

HRID 2080181Notes

Reaction equation

HRID 2080181 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]([CH2:11][O:12][CH3:13])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[F:14][C:15]1[CH:30]=[CH:29][C:18]([CH2:19][O:20][C:21]2[CH:28]=[CH:27][C:24]([CH2:25][NH2:26])=[CH:23][CH:22]=2)=[CH:17][CH:16]=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>CN(C)C=O.O>[NH2:1][C:2]1[N:10]=[C:9]([CH2:11][O:12][CH3:13])[CH:8]=[CH:7][C:3]=1[C:4]([NH:26][CH2:25][C:24]1[CH:27]=[CH:28][C:21]([O:20][CH2:19][C:18]2[CH:29]=[CH:30][C:15]([F:14])=[CH:16][CH:17]=2)=[CH:22][CH:23]=1)=[O:6]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 64866744-(4-Fluoro-benzyloxy)-benzylamineHCID 231304372-Amino-6-methoxymethylnicotinic acid

Product 1

HCID 231305542-Amino-N-(4-(4-fluoro-benzyloxy)-benzyl)-6-methoxymethyl-nicotinamideYield 60%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-amino-6-methoxymethyl-nicotinic acid described in Preparation Example A-11 (10 mg, 0.055 mmol) and 4-(4-fluoro-benzyloxy)-benzylamine described in Preparation Example 155 (19 mg, 0.082 mmol) in N,N-dimethylformamide (1 mL) were added benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (29 mg, 0.066 mmol) and triethylamine (0.022 mL, 0.16 mmol), and the solution was stirred overnight at room temperature. Water was added to the reaction solution, the precipitated solid was filtered, and the title compound (13 mg, 0.033 mmol, 60%) was obtained as a colorless solid.

Workup

  1. filtrationthe precipitated solid was filtered

Sources & evidence

ORD record
ord-7054defe393149a792676bb55fd881e8
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

Loading…