Diethylamine → HCID 68835403, compound

HRID 2112937Notes

Reaction equation

HRID 2112937 reaction equation
[CH2:1]([NH:3][CH2:4][CH3:5])[CH3:2].C[Al](C)C.C(O[C:13]([C:15]1[N:20]2[N:21]=[C:22]([NH:24][C:25]([NH:27][CH2:28][CH3:29])=[O:26])[N:23]=[C:19]2[CH:18]=[C:17]([C:30]2[CH:31]=[N:32][CH:33]=[CH:34][CH:35]=2)[CH:16]=1)=[O:14])C.[Na].C(C(C(C([O-])=O)O)O)([O-])=O.[K+].[K+]>O1CCCC1.CCCCCCC.C(OCC)(=O)C>[CH2:1]([N:3]([CH2:4][CH3:5])[C:13]([C:15]1[N:20]2[N:21]=[C:22]([NH:24][C:25]([NH:27][CH2:28][CH3:29])=[O:26])[N:23]=[C:19]2[CH:18]=[C:17]([C:30]2[CH:31]=[N:32][CH:33]=[CH:34][CH:35]=2)[CH:16]=1)=[O:14])[CH3:2]

Participants

8

Reactant 4

HCID 8021DiethylamineHCID 16682925TrimethylaluminumHCID 57643109HCID 57643109, compoundHCID 86594854CID 86594854

Product 1

HCID 68835403HCID 68835403, compound

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolventHCID 8900HeptaneSolvent

Procedure

Diethylamine (0.400 mL) was suspended in tetrahydrofuran (2.00 mL) and cooled in an ice bath. This solution was charged with trimethylaluminum (0.500 mL of a 2 M solution in heptane). After 20 minutes the reaction was charged with the 2-(3-ethyl-ureido)-7-pyridin-3-yl-[1,2,4]triazolo[1,5-a]pyridine-5-carboxylic acid ethyl ester, prepared as in Example 16, Step 1, (0.255 g, 0.720 mmol) and shaken. After 18 hours the reaction was diluted with 1 volume of ethyl acetate and treated with an equal amount saturated aqueous sodium/potassium tartrate. After 6 hours the organic layer was isolated, dried over magnesium sulfate and concentrated to afford the desired product 2-(3-ethyl-ureido)-7-pyridin-3-yl-[1,2,4]triazolo[1,5-a]pyridine-5-carboxylic acid diethylamide, MS (APCI+): m/z 382.1 (M+H).

Workup

  1. temperaturecooled in an ice bath
  2. customAfter 6 hours the organic layer was isolated
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-290dfeb3b9f94566859ff202ab3ad8cb
Source dataset
uspto-grants-2009_04
Patent number
US07524860B2

Reaction notes

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