phenyl 3-(1-methyl-1H-tetraazol-5-yl)phenylcarbamate → HCID 69039811, compound

HRID 1454249Notes

Reaction equation

HRID 1454249 reaction equation
[F:1][C:2]1[CH:20]=[CH:19][C:5]([CH2:6][N:7]2[CH2:12][CH2:11][CH2:10][C@@:9]3([CH2:17][CH2:16][CH2:15][CH2:14][C@H:13]3[NH2:18])[CH2:8]2)=[CH:4][CH:3]=1.C1([O:27][C:28](=O)[NH:29][C:30]2[CH:35]=[CH:34][CH:33]=[C:32]([C:36]3[N:40]([CH3:41])[N:39]=[N:38][N:37]=3)[CH:31]=2)C=CC=CC=1>O1CCCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[CH2:12][CH2:11][CH2:10][C@@:9]3([CH2:17][CH2:16][CH2:15][CH2:14][C@H:13]3[NH:18][C:28]([NH:29][C:30]3[CH:35]=[CH:34][CH:33]=[C:32]([C:36]4[N:40]([CH3:41])[N:39]=[N:38][N:37]=4)[CH:31]=3)=[O:27])[CH2:8]2)=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 22252681phenyl 3-(1-methyl-1H-tetraazol-5-yl)phenylcarbamateHCID 69040338HCID 69040338, compound

Product 1

HCID 69039811HCID 69039811, compoundYield 52.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (6S,7R)-2-(4-fluorobenzyl)-2-aza-spiro[5.5]undec-7-ylamine (90 mg, 0.32 mmol) in tetrahydrofuran (2 mL) was treated with [3-(1-methyl-1H-tetrazol-5-yl)-phenyl]-carbamic acid phenyl ester (123 mg, 0.42 mmol), and the mixture was stirred at room temperature overnight. The solvent was removed under vacuum and the resulting solid was purified by chromatography on silica gel, eluting with 0.2:1.8:98 ammonium hydroxide/methanol/dichloromethane, to give the desired product (80 mg). 1H NMR (300 MHz, CDCl3) δ8.27 (bs, 1H), 7.94 (d, J=9 Hz, 1H), 7.82 (bs, 1H), 7.39 (t, J=8 Hz, 1H), 7.26-7.19 (m, 3H), 6.98-6.91 (m, 2H), 6.21 (bs, 1H), 4.17 (s, 3H), 3.98 (bs, 1H), 3.35 (m, 2H), 2.50-2.15 (m, 3H), 1.85 (m, 2H), 1.65-1.20 (m, 11H). Mass spec (ES+) m+/z 478.4 (M+H+).

Workup

  1. customThe solvent was removed under vacuum
  2. customthe resulting solid was purified by chromatography on silica gel
  3. washeluting with 0.2:1.8:98 ammonium hydroxide/methanol/dichloromethane

Sources & evidence

ORD record
ord-76f0ac9b8d814e4eb75aebb47040ad77
Source dataset
uspto-grants-2009_01
Patent number
US07479496B2

Reaction notes

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