Dichloromethane → HCID 178505100, compound

HRID 1641310Notes

Reaction equation

HRID 1641310 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].NCCCCC[CH2:12][O:13][C:14]1[CH:15]=[C:16]([CH:43]=[CH:44][CH:45]=1)[CH2:17][N:18]1[CH2:42][CH2:41][C:21]2([N:25]([C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([F:32])[CH:27]=3)[C:24](=[O:33])[N:23]=[C:22]2[NH:34][CH:35]2[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]2)[CH2:20][CH2:19]1.CC[N:48]([CH2:51][CH3:52])CC.[CH2:53](Cl)Cl>>[CH:35]1([NH:34][C:22]2[C:21]3([CH2:20][CH2:19][N:18]([CH2:17][C:16]4[CH:15]=[C:14]([CH:45]=[CH:44][CH:43]=4)[O:13][CH2:12][CH2:53][CH2:52][CH2:51][NH:48][S:2]([CH3:1])(=[O:4])=[O:3])[CH2:42][CH2:41]3)[N:25]([C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([F:32])[CH:27]=3)[C:24](=[O:33])[N:23]=2)[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40]1

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 178510990HCID 178510990, compound

Product 1

HCID 178505100HCID 178505100, compound

Procedure

Methanesulfonyl chloride (0.019 mL, 0.245 mmole) was added dropwise to a solution of 8-{3-[(6-aminohexyl)oxy]benzyl}-4-(cyclohexylamino)-1-(3-fluorophenyl)-1,3,8-triazaspiro[4.5]dec-3-en-2-one (0.116 mg, 0.222 mmole) in 5 mL CH2Cl2 at rt, and Et3N (0.034 mL, 0.245 mmole. After stirring for 0.5 hr at rt, the reaction was concentrated in vacuo. The residue was redissolved in CH2Cl2, washed with H2O, and then brine. Dried over Na2SO4, filtered and conc in vacuo. The residue was purified on a 40 g silica gel column eluting with 100% CH2Cl2 saturated with ammonia to 4% MeOH in CH2Cl2 saturated with ammonia. The clean fractions were combined and concentrated in vacuo to yield the product.

Workup

  1. concentrationthe reaction was concentrated in vacuo
  2. dissolutionThe residue was redissolved in CH2Cl2
  3. washwashed with H2O
  4. dry with materialDried over Na2SO4
  5. filtrationfiltered and conc in vacuo
  6. customThe residue was purified on a 40 g silica gel column
  7. washeluting with 100% CH2Cl2 saturated with ammonia to 4% MeOH in CH2Cl2 saturated with ammonia
  8. concentrationconcentrated in vacuo
  9. customto yield the product

Sources & evidence

ORD record
ord-3f9b12352a9a48cdb56054eb4fec9e59
Source dataset
uspto-grants-2012_02
Patent number
US08114887B2

Reaction notes

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