Sodium Azide → HCID 86603408, compound

HRID 1994475Notes

Reaction equation

HRID 1994475 reaction equation
CS(O[CH:6]([C:38]1[CH:43]=[C:42]([C:44]([F:47])([F:46])[F:45])[CH:41]=[C:40]([C:48]([F:51])([F:50])[F:49])[CH:39]=1)[CH2:7][N:8]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:9][C:10]1[CH:15]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:13]=[CH:12][C:11]=1[C:20]1[CH:25]=[C:24]([CH:26]([CH3:28])[CH3:27])[CH:23]=[CH:22][C:21]=1[O:29][CH3:30])(=O)=O.[N-:52]=[N+:53]=[N-:54].[Na+]>CN1C(=O)N(C)CCC1.CCOC(C)=O>[C:34]([O:33][C:31](=[O:32])[N:8]([CH2:7][CH:6]([N:52]=[N+:53]=[N-:54])[C:38]1[CH:43]=[C:42]([C:44]([F:47])([F:46])[F:45])[CH:41]=[C:40]([C:48]([F:49])([F:50])[F:51])[CH:39]=1)[CH2:9][C:10]1[CH:15]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:13]=[CH:12][C:11]=1[C:20]1[CH:25]=[C:24]([CH:26]([CH3:27])[CH3:28])[CH:23]=[CH:22][C:21]=1[O:29][CH3:30])([CH3:36])([CH3:37])[CH3:35]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 86603406HCID 86603406, compound

Product 1

HCID 86603408HCID 86603408, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-Solvent

Procedure

The 1-[3,5-bis(trifluoromethyl)phenyl]-2-((tert-butoxycarbonyl){[5′-isopropyl-2′-methoxy-4-(trifluoromethyl)biphenyl-2-yl]methyl}amino)ethyl methanesulfonate from the previous reaction was dissolved in DMPU (15 mL) and treated with NaN3 (140 mg, 2.15 mmol). The reaction was stirred at room temperature for 15 hours and then diluted with EtOAc (75 ml). The solution was washed with H2O (5×40 mL) and brine (40 mL). The organic layer was dried over Na2SO4, filtered, and concentrated. The residue was purified with 20% EtOAc/hexanes to afford tert-butyl{2-azido-2-[3,5-bis(trifluoromethyl)phenyl]ethyl}{[5′-isopropyl-2′-methoxy-4-(trifluoromethyl)biphenyl-2-yl]methyl}carbamate. Rf=0.52 (15% EtOAc/hexanes). LCMS=605.3 (M+1-BOC)+. 1H NMR (C6D6, 500 MHz, 70° C.) δ 7.80 (s, 1H), 7.67 (s, 1H), 7.48 (s, 2H), 7.36 (d, J=7.8 Hz, 1H), 7.01-7.11 (m, 2H), 6.89 (m, 1H), 6.64 (d, J=8.6 Hz, 1H), 4.22-4.69 (m, 3H), 3.28 (s, 3H), 2.61-3.16 (m, 3H), 1.34 (s, 9H), 1.13-1.18 (m, 6H).

Workup

  1. washThe solution was washed with H2O (5×40 mL) and brine (40 mL)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified with 20% EtOAc/hexanes

Sources & evidence

ORD record
ord-a648fa1b0c5d4f5085cd49c239226d02
Source dataset
uspto-grants-2010_01
Patent number
US07652049B2

Reaction notes

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