Imidazole → HCID 57989134, compound

HRID 1689547Notes

Reaction equation

HRID 1689547 reaction equation
O[CH2:2][CH:3]([CH3:32])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][N:11]1[CH2:31][CH2:30][C:14]2([O:19][CH2:18][CH2:17][N:16]([C:20]([C:22]3[N:23]=[C:24]([CH:27]([CH3:29])[CH3:28])[S:25][CH:26]=3)=[O:21])[CH2:15]2)[CH2:13][CH2:12]1.C(Br)(Br)(Br)[Br:34].N1C=CN=C1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl.O>[Br:34][CH2:2][CH:3]([CH3:32])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][N:11]1[CH2:31][CH2:30][C:14]2([O:19][CH2:18][CH2:17][N:16]([C:20]([C:22]3[N:23]=[C:24]([CH:27]([CH3:29])[CH3:28])[S:25][CH:26]=3)=[O:21])[CH2:15]2)[CH2:13][CH2:12]1

Participants

7

Reactant 4

HCID 795ImidazoleHCID 11205Carbon tetrabromide2×HCID 11776Triphenylphosphine2×HCID 57989057HCID 57989057, compound

Product 1

HCID 57989134HCID 57989134, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent3×

Conditions

Temperature
0 °C

Procedure

(9-(9-Hydroxy-8-methylnonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-isopropylthiazol-4-yl)methanone (example 283, step b) (100 mg), carbon tetrabromide (143 mg) and imidazole (30 mg) were dissolved in DCM (5 mL). The solution was cooled to 0° C. and a solution of triphenylphosphine (85 mg) in DCM (1 mL) was added dropwise. The reaction mixture was stirred at this temperature for 1 hour then at room temperature for 2 hours. A further amount of carbon tetrabromide (150 mg) was added, the mixture cooled to 0° C. and triphenylphosphine (114 mg) in DCM (1 mL) added dropwise. Stirred at room temperature for 1 hour then water was added and the phases separated. The organic phase was evaporated and the product purified by silica gel chromatography eluting with 0-10% methanol in DCM to afford the subtitled compound as an orange gum. Yield 0.088 g.

Workup

  1. waitat room temperature for 2 hours
  2. temperaturethe mixture cooled to 0° C.
  3. stirringStirred at room temperature for 1 hour
  4. customthe phases separated
  5. customThe organic phase was evaporated
  6. customthe product purified by silica gel chromatography
  7. washeluting with 0-10% methanol in DCM

Sources & evidence

ORD record
ord-a41651830cd74717ae5bd462939c0082
Source dataset
uspto-grants-2012_04
Patent number
US08148373B2

Reaction notes

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