1,2-Dichloroethane → 3-Butyl-imidazo[1,5-a]pyridine-1-carboxylic acid adamantan-1-ylamide

HRID 1783778Notes

Reaction equation

HRID 1783778 reaction equation
[CH2:1]([C:5]1[N:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]2=[C:7]([C:14]([OH:16])=O)[N:6]=1)[CH2:2][CH2:3][CH3:4].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CCN(CC)CC.[C:38]12([NH2:48])[CH2:47][CH:42]3[CH2:43][CH:44]([CH2:46][CH:40]([CH2:41]3)[CH2:39]1)[CH2:45]2>CN(C=O)C.C(OCC)(=O)C>[C:38]12([NH:48][C:14]([C:7]3[N:6]=[C:5]([CH2:1][CH2:2][CH2:3][CH3:4])[N:9]4[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=34)=[O:16])[CH2:45][CH:44]3[CH2:43][CH:42]([CH2:41][CH:40]([CH2:46]3)[CH2:39]1)[CH2:47]2

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 2130AmantadineHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 249483973-Butyl-imidazo[1,5-a]pyridine-1-carboxylic acid

Product 1

HCID 249482053-Butyl-imidazo[1,5-a]pyridine-1-carboxylic acid adamantan-1-ylamideYield 80%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-butyl-imidazo[1,5-a]pyridine-1-carboxylic acid (150 mg, 0.56 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 (157 mg, 80%). 1H NMR (DMSO-d6) δ 8.31 (1H), 8.02 (1H), 7.04 (1H), 6.93 (1H), 6.81 (1H), 2.99 (2H), 2.08 (9H), 1.67 (8H), 1.38 (2H), 0.92 (3H); m/z (M+H)=352.1.

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-a33590c1095a438a9ae560b58fdf0d6a
Source dataset
uspto-grants-2009_03
Patent number
US07501438B2

Reaction notes

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