Diisopropylethylamine → HCID 15616388, compound

HRID 703421Notes

Reaction equation

HRID 703421 reaction equation
Cl.Cl.[NH2:3][CH:4]1[CH:9]2[CH2:10][CH2:11][N:6]([CH2:7][CH2:8]2)[CH2:5]1.[N:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18]([NH:20][C:21](N)=[O:22])=[O:19].C(N(C(C)C)CC)(C)C>N1C=CC=CC=1>[N:6]12[CH2:11][CH2:10][CH:9]([CH2:8][CH2:7]1)[CH:4]([NH:3][C:21]([NH:20][C:18]([C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][N:12]=1)=[O:19])=[O:22])[CH2:5]2

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 197853Quinuclidine, 3-amino-, dihydrochlorideHCID 287116HCID 287116, compound

Product 1

HCID 15616388HCID 15616388, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

The above compound was prepared, following the procedure of Example 14b, from 3-aminoquinuclidine dihydrochloride(1.0 g, 5 mmol), 2-pyridoylurea (0.82 g, 5 mmol) and di-isopropylethylamine (1.3 g, 10 mmol) in pyridine (20 ml) by refluxing for 4 days. The pyridine was evaporated and the residue partitioned between ether and 10% aqueous w/v citric acid. The mixture was filtered, the aqueous phase washed with ether, then basified with potassium carbonate to precipitate the title compound (0.60 g) which was converted to the 1:1 fumarate, mp 202°-203° C.

Workup

  1. customThe above compound was prepared
  2. customThe pyridine was evaporated
  3. customthe residue partitioned between ether and 10% aqueous w/v citric acid
  4. filtrationThe mixture was filtered
  5. washthe aqueous phase washed with ether
  6. customto precipitate the title compound (0.60 g) which

Sources & evidence

ORD record
ord-6c5c57195731430ba9ae7a234fe3d815
Source dataset
uspto-grants-1991_01
Patent number
US04983600

Reaction notes

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