Sodium hydride → HCID 68549442, compound

HRID 1446100Notes

Reaction equation

HRID 1446100 reaction equation
Br[C:2]1[N:3]([CH2:10][C:11]([CH3:28])([OH:27])[CH2:12][N:13]2[CH2:19][CH2:18][CH2:17][N:16]([C:20]3[N:25]=[CH:24][C:23]([Br:26])=[CH:22][N:21]=3)[CH2:15][CH2:14]2)[CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=1.[H-].[Na+]>CN(C=O)C.[NH4+].[Cl-]>[Br:26][C:23]1[CH:22]=[N:21][C:20]([N:16]2[CH2:17][CH2:18][CH2:19][N:13]([CH2:12][C:11]3([CH3:28])[O:27][C:2]4=[N:6][C:5]([N+:7]([O-:9])=[O:8])=[CH:4][N:3]4[CH2:10]3)[CH2:14][CH2:15]2)=[N:25][CH:24]=1

Participants

5

Reactant 2

HCID 24758Sodium hydrideHCID 68548350HCID 68548350, compound

Product 1

HCID 68549442HCID 68549442, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 25517Ammonium ChlorideSolvent

Conditions

Temperature
60 °C

Procedure

The 1-(2-Bromo-4-nitro-imidazol-1-yl)-3-[4-(5-bromo-pyrimidin-2-yl)-[1,4]diazepan-1-yl]-2-methyl-propan-2-ol (600 mg, 1.15 mmol) in DMF (4 ml) was treated with NaH (33 mg, 1.4 mmol) at 0° C. and heated to 60° C. for 2 h. The reaction mixture is cooled, diluted with saturated NH4Cl (aq) and extracted with EtOAc. The organic layer was dried over Na2SO4, concentrated and purified by column chromatography to titled compound (384 mg, 75%). ESI MS m/z 439 (M+H+); 1H NMR (400 MHz, CDCl3) δ 8.24 (s, 2H), 7.4 (s, 1H) 4.15 (d, J=23 Hz, 1H), 3.81 (m, 5H), 3.06 (d, J=38 Hz, 1H), 2.95 (m, 2H), 2.85 (m, 1H), 2.75 (m, 1H), 2.62 (d, J=29 Hz, 1H), 1.63 (m, 2H), 1.54 (s, 3H).

Workup

  1. temperatureThe reaction mixture is cooled
  2. extractionextracted with EtOAc
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated
  5. custompurified by column chromatography to titled compound (384 mg, 75%)

Sources & evidence

ORD record
ord-1947fed001f347ff8c89188f91e77657
Source dataset
uspto-grants-2010_02
Patent number
US07666864B2

Reaction notes

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