1,2-Dichloroethane → HCID 24948784, compound

HRID 1783799Notes

Reaction equation

HRID 1783799 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]CC.C(Cl)CCl.C1C=CC2N([OH:30])N=NC=2C=1.C([N:33]([CH:37]([CH3:39])C)[CH:34]([CH3:36])C)C.[NH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1>CN(C=O)C.C(OCC)(=O)C>[C:41]1([NH:40][C:14]([C:7]2[N:6]=[C:5]([CH2:1][CH2:2][N:33]3[CH2:34][CH2:36][O:30][CH2:39][CH2:37]3)[N:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=23)=[O:16])[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 6115AnilineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 249483973-Butyl-imidazo[1,5-a]pyridine-1-carboxylic acid

Product 1

HCID 24948784HCID 24948784, compoundYield 16%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-butyl-imidazo[1,5-a]pyridine-1-carboxylic acid (200 mg, 0.73 mmol) in DMF (5 mL) was added EDC (182 mg, 0.95 mmol), HOBt, (129 mg, 0.95 mmol) and iPr2EtN (0.22 mL, 1.31 mmol). The mixture was allowed to stir for 10 min. and aniline (0.080 mL, 0.88 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 (40 mg, 16%). 1H NMR (DMSO-d6) δ 9.72 (1H), 8.41 (1H), 8.15 (1H), 7.83 (2H), 7.30 (2H), 7.18 (1H), 7.05 (1H), 6.95 (1H), 3.58 (4H), 3.25 (2H), 2.80 (2H), 2.48 (4H); m/z (M+H)=351.15.

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-72c381f4ae17497ea9d0f6d9784fd8ee
Source dataset
uspto-grants-2009_03
Patent number
US07501438B2

Reaction notes

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