Pivaloyl chloride → HCID 11615563, compound

HRID 650539Notes

Reaction equation

HRID 650539 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][C:9](C=O)=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1.[NH:13]1[CH2:17][CH:16]=[CH:15][CH2:14]1.[C:18](C1NC=CN=1)(C1NC=CN=1)=[O:19].C([NH+](CC)CC)C.CC(C)(C)C(Cl)=O>>[O:4]1[C:5]2[CH:10]=[CH:9][CH:8]=[C:7]([C:18]([N:13]3[CH2:17][CH:16]=[CH:15][CH2:14]3)=[O:19])[C:6]=2[O:1][CH2:2][CH2:3]1

Participants

6

Reactant 5

HCID 62493Pivaloyl chlorideHCID 660593-PyrrolineHCID 2481272,3-Dihydro-1,4-benzodioxin-6-carbaldehydeHCID 1385867TriethylammoniumHCID 5250894Bis-(1H-imidazol-2-YL)-methanone

Product 1

HCID 11615563HCID 11615563, compound

Procedure

1,4-Benzodioxan-6-carboxaldehyde is oxidized to the corresponding acid by the procedure of Shriner and Kleiderer in Organic Syntheses, Coll. Vol. 2:538 (1943). Coupling of the acid with 3-pyrroline is conducted by employing the same method as employed for the preparation of Invention Compound V, which uses carbonyl diimidazole in order to activate the carboxylic acid, or any other method known in the art, such as, for example, activation by the reaction of the triethylammonium salt with trimethylacetyl chloride. The product is crystallized from CCl4/Et2O/hexanes. EMIS m/z=231 (parent), 163 (base), 135, and 107. 1H NMR δ 4.25-4.30 (m, 6), 4.43 (br, 2), 5.75 (m, 1), 5.85 (m, 1), 6.88 (d, 1, J=8.42 Hz), 7.06 (dd, 1, J=8.38, 2.03 Hz), and 7.09 (d, 1, J=2.05 Hz).

Workup

  1. customThe product is crystallized from CCl4/Et2O/hexanes

Sources & evidence

ORD record
ord-5684c90fe7e948d6ad457241be046c99
Source dataset
uspto-grants-2001_08
Patent number
US06274600B1

Reaction notes

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