2,4,6-Trimethylpyridine → HCID 178521852, compound

HRID 706668Notes

Reaction equation

HRID 706668 reaction equation
CCN=C=NCCCN(C)C.CC1C=C(C)C=C(C)N=1.[OH:21][C:22]1[CH:27]=[CH:26][N:25]2[C:28]([C:31]([OH:33])=O)=[CH:29][N:30]=[C:24]2[CH:23]=1.[CH2:34]([N:41]1[C:49]2[CH:48]=[CH:47][CH:46]=[C:45]([NH2:50])[C:44]=2[CH:43]=[N:42]1)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>CN(C=O)C.CCOC(C)=O>[CH2:34]([N:41]1[C:49]2[C:44](=[C:45]([NH:50][C:31]([C:28]3[N:25]4[CH:26]=[CH:27][C:22]([OH:21])=[CH:23][C:24]4=[N:30][CH:29]=3)=[O:33])[CH:46]=[CH:47][CH:48]=2)[CH:43]=[N:42]1)[C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1

Participants

7

Reactant 4

HCID 79532,4,6-TrimethylpyridineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 213273171-benzyl-1H-indazol-4-amineHCID 178524732HCID 178524732, compound

Product 1

HCID 178521852HCID 178521852, compoundYield 0.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A suspension of EDCI (192 mg, 0.679 mmol), 2,4,6-trimethylpyridine (224 mg, 1.85 mmol), and 7-hydroxyimidazo[1,2-a]pyridine-3-carboxylic acid (110 mg, 0.617 mmol) in DMF (2 mL) was stirred at ambient temperature for two hours. A solution of 1-benzyl-1H-indazol-4-amine (138 mg, 0.617 mmol) in DMF (2 mL) was added, and the resulting mixture was sonicated for 5 minutes. The heterogeneous mixture was stirred at ambient temperature overnight, then diluted with EtOAc, and washed twice with 1M aqueous hydrochloric acid, followed by brine. The organic layer was concentrated and subjected to chromatography on silica with 10% MeOH/DCM as eluent to provide 1.5 mg of desired product. MS (ES+APCI) m/z=384 (M+H) detected.

Workup

  1. customthe resulting mixture was sonicated for 5 minutes
  2. stirringThe heterogeneous mixture was stirred at ambient temperature overnight
  3. washwashed twice with 1M aqueous hydrochloric acid
  4. concentrationThe organic layer was concentrated

Sources & evidence

ORD record
ord-e0c0651fdc1949d79f85b7fabc7844fc
Source dataset
uspto-grants-2015_11
Patent number
US09174981B2

Reaction notes

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