Diisopropylethylamine → HCID 66816696, compound

HRID 1755021Notes

Reaction equation

HRID 1755021 reaction equation
C([N:4](CC)C(C)C)(C)C.[I-].ClC1C=CC=C[N+]=1C.[CH3:19][C:20]1[CH:21]=[C:22]([CH2:49][C:50]([OH:52])=O)[CH:23]=[CH:24][C:25]=1/[CH:26]=[CH:27]/[S:28]([N:31]1[CH2:48][CH2:47][C:34]2([N:38]=[C:37]([CH:39]3[CH2:44][CH2:43][CH:42]([CH3:45])[CH2:41][CH2:40]3)[NH:36][C:35]2=[O:46])[CH2:33][CH2:32]1)(=[O:30])=[O:29].N.CO>ClCCl.CN(C=O)C.CN(C1C=CN=CC=1)C>[CH3:19][C:20]1[CH:21]=[C:22]([CH2:49][C:50]([NH2:4])=[O:52])[CH:23]=[CH:24][C:25]=1/[CH:26]=[CH:27]/[S:28]([N:31]1[CH2:48][CH2:47][C:34]2([N:38]=[C:37]([CH:39]3[CH2:40][CH2:41][CH:42]([CH3:45])[CH2:43][CH2:44]3)[NH:36][C:35]2=[O:46])[CH2:33][CH2:32]1)(=[O:30])=[O:29]

Participants

8

Reactant 4

HCID 81531DiisopropylethylamineHCID 1670692-Chloro-1-methylpyridinium iodideHCID 21705897Ammonia methanolHCID 66817739HCID 66817739, compound

Product 1

HCID 66816696HCID 66816696, compoundYield 61%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

N,N-Diisopropylethylamine (31.4 μL, 0.185 mmol) and 2-chloro-1-methylpyridinium iodide (18.9 mg, 0.074 mmol) were added to a solution of (3-methyl-4-{(E)-2-[2-(4-methyl-cyclohexyl)-4-oxo-1,3,8-triaza-spiro[4.5]dec-1-ene-8-sulfonyl]-vinyl}-phenyl)-acetic acid (30.0 mg, 0.062 mmol) in dichloromethane (0.5 mL) and DMF (0.1 mL), and the mixture was stirred for 10 minutes. A 2.0 M ammonia-methanol solution (0.15 mL, 0.308 mmol) and DMAP (0.8 mg, 0.006 mmol) were then added, and the mixture was stirred overnight. The reaction mixture was then quenched by adding a saturated aqueous ammonium chloride solution and extracted with ethyl acetate. The organic layer was sequentially washed with water and saturated brine, and then dried over anhydrous Na2SO4 and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to give 2-(3-methyl-4-{(E)-2-[2-(4-methyl-cyclohexyl)-4-oxo-1,3,8-triaza-spiro[4.5]dec-1-ene-8-sulfonyl]-vinyl}-phenyl)-acetamide as a white powder (18.3 mg, 61%).

Workup

  1. stirringthe mixture was stirred overnight
  2. customThe reaction mixture was then quenched
  3. additionby adding a saturated aqueous ammonium chloride solution
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was sequentially washed with water and saturated brine
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationconcentrated under reduced pressure
  8. customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-2b4922818f2349db8186f95277d9747d
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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