1,2-Dichloroethane → HCID 24948022, compound

HRID 1783775Notes

Reaction equation

HRID 1783775 reaction equation
[C:1]1([C:11]2[N:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:14]3=[C:13]([C:20]([OH:22])=O)[N:12]=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CCN(CC)CC.[C:44]12([NH2:54])[CH2:53][CH:48]3[CH2:49][CH:50]([CH2:52][CH:46]([CH2:47]3)[CH2:45]1)[CH2:51]2>CN(C=O)C.C(OCC)(=O)C>[C:44]12([NH:54][C:20]([C:13]3[N:12]=[C:11]([C:1]4[C:10]5[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=5)[CH:4]=[CH:3][CH:2]=4)[N:15]4[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=34)=[O:22])[CH2:51][CH:50]3[CH2:49][CH:48]([CH2:47][CH:46]([CH2:52]3)[CH2:45]1)[CH2:53]2

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 2130AmantadineHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 249480213-Naphthalen-1-yl-imidazo[1,5-a]pyridine-1-carboxylic acid

Product 1

HCID 24948022HCID 24948022, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-naphthalen-1-yl-imidazo[1,5-a]pyridine-1-carboxylic acid (55 mg, 0.19 mmol) in DMF (5 mL) was added EDC (161 mg, 0.84 mmol), HOBt, (90 mg, 0.67 mmol) and Et3N (0.23 mL, 1.68 mmol). The mixture was allowed to stir for 10 min. and adamantylamine (93 mg, 0.62 mmol) was added. The mixture was stirred for 15 h then diluted with ethyl acetate (30 mL) and washed with water (50 mL). The organic layer was dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was chromatographed on silica to yield the title compound (67 mg, 84%).

Workup

  1. stirringThe mixture was stirred for 15 h
  2. washwashed with water (50 mL)
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was chromatographed on silica

Sources & evidence

ORD record
ord-e8232e22aa0943378d95c5c298ee9d59
Source dataset
uspto-grants-2009_03
Patent number
US07501438B2

Reaction notes

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