Methanol → 3-fluoro-5-(4-methylpiperidin-1-yl)-N-[4-(2H-tetrazol-5-ylmethoxy)-naphthalen-1-yl]-benzamide

HRID 1171423Notes

Reaction equation

HRID 1171423 reaction equation
[C:1]([CH2:3][O:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([NH:15][C:16](=[O:31])[C:17]2[CH:22]=[C:21]([N:23]3[CH2:28][CH2:27][CH:26]([CH3:29])[CH2:25][CH2:24]3)[CH:20]=[C:19]([F:30])[CH:18]=2)=[CH:7][CH:6]=1)#[N:2].C[Si]([N:36]=[N+:37]=[N-:38])(C)C.C([Sn](=O)CCCC)CCC.CO>C1(C)C=CC=CC=1>[F:30][C:19]1[CH:18]=[C:17]([CH:22]=[C:21]([N:23]2[CH2:24][CH2:25][CH:26]([CH3:29])[CH2:27][CH2:28]2)[CH:20]=1)[C:16]([NH:15][C:8]1[C:9]2[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:5]([O:4][CH2:3][C:1]2[N:36]=[N:37][NH:38][N:2]=2)=[CH:6][CH:7]=1)=[O:31]

Participants

6

Reactant 4

HCID 887MethanolHCID 61221Dibutyltin oxideHCID 78378AzidotrimethylsilaneHCID 59553169HCID 59553169, compound

Product 1

HCID 595530853-fluoro-5-(4-methylpiperidin-1-yl)-N-[4-(2H-tetrazol-5-ylmethoxy)-naphthalen-1-yl]-benzamideYield 0%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

N-(4-Cyanomethoxynaphthalen-1-yl)-3-fluoro-5-(4-methylpiperidin-1-yl)-benzamide (54 mg, 129 mmol), trimethylsilylazide (0.1 ml, 760 mmol) and dibutyltin oxide (5 mg) are heated to reflux in anhydrous toluene (3 ml) for 5 hours. After cooling to room temperature methanol (5 ml) is then added and the mixture stirred at room temperature for 30 min. The mixture is then evaporated to dryness and the residue recrystallized from ethyl acetate/hexanes to give 3-fluoro-5-(4-methylpiperidin-1-yl)-N-[4-(2H-tetrazol-5-ylmethoxy)-naphthalen-1-yl]-benzamide as a grey powder (22 mg). 1H NMR 300 MHz (DMSO-d6) 10.3 (s, 1H), 8.32 (dd, 1H, J=8.7 and 2.7 Hz), 7.87 (d, 1H, J=9.3 Hz), 7.54-7.62 (m, 2H), 7.42-7.5 (m, 2H), 7.17 (dd, 1H, J=15.9 and 9.3 Hz), 6.97 (d, 1H, J=13.2 Hz), 5.7 (s, 2H), 3.85 (d, 2H, J=19.8 Hz), 2.77 (m, 2H), 1.5-1.78 (m, 3H), 1.25 (m, 2H), 0.95 (d, 3H, J=6.6 Hz).

Workup

  1. additionis then added
  2. customThe mixture is then evaporated to dryness
  3. customthe residue recrystallized from ethyl acetate/hexanes

Sources & evidence

ORD record
ord-5186335845f24766b96b97933f4dd126
Source dataset
uspto-grants-2010_11
Patent number
US07829560B2

Reaction notes

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