phenyl 3-(1-methyl-1H-tetraazol-5-yl)phenylcarbamate → HCID 58997671, compound

HRID 1592323Notes

Reaction equation

HRID 1592323 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:19][C@@H:20]1[CH2:25][CH2:24][CH2:23][CH2:22][C@H:21]1[NH2:26])[CH2:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:27][N:28]1[C:32]([C:33]2[CH:34]=[C:35]([NH:39][C:40](=O)[O:41]C3C=CC=CC=3)[CH:36]=[CH:37][CH:38]=2)=[N:31][N:30]=[N:29]1>CN(C=O)C>[C:1]([O:5][C:6]([N:8]([CH2:19][C@@H:20]1[CH2:25][CH2:24][CH2:23][CH2:22][C@H:21]1[NH:26][C:40]([NH:39][C:35]1[CH:36]=[CH:37][CH:38]=[C:33]([C:32]2[N:28]([CH3:27])[N:29]=[N:30][N:31]=2)[CH:34]=1)=[O:41])[CH2:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 22252681phenyl 3-(1-methyl-1H-tetraazol-5-yl)phenylcarbamateHCID 58997640HCID 58997640, compound

Product 1

HCID 58997671HCID 58997671, compoundYield 25.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The product of Step i (0.26 g, 0.69 mmol, 1 eq.), and phenyl 3-(1-methyl-1H-tetraazol-5-yl)phenylcarbamate (Example 1a, see below)(0.20 g, 0.69 mmol, 1 eq.) were dissolved in DMF (2 mL) at room temperature and stirred under N2 overnight. The DMF was stripped on the rotary evaporator and EtOAc was added (50 mL). This mixture was washed with water (3×50 mL), dried (MgSO4), stripped, and flash chromatographed in 3:1 Hexanes/EtOAc to 1:1 Hexanes/EtOAc to 100% EtOAc to yield 98 mg of a white glass. MS (AP+) detects (M+H)+=566.6.

Workup

  1. customThe DMF was stripped on the rotary evaporator and EtOAc
  2. additionwas added (50 mL)
  3. washThis mixture was washed with water (3×50 mL)
  4. dry with materialdried (MgSO4)
  5. customflash chromatographed in 3:1 Hexanes/EtOAc to 1:1 Hexanes/EtOAc to 100% EtOAc

Sources & evidence

ORD record
ord-99ead3181db8492cb332502a6d559a73
Source dataset
uspto-grants-2007_11
Patent number
US07291744B2

Reaction notes

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