Imidazo(4,3-b)(1,3)thiazole-7-carbaldehyde → 7-[[5-(Morpholin-4-yl)methylpyridin-3-yl]hydroxymethyl]imidazo[5,1-b]thiazole

HRID 1072345Notes

Reaction equation

HRID 1072345 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH2:8][N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)[CH:5]=[N:6][CH:7]=1.[CH:15]([C:17]1[N:18]=[CH:19][N:20]2[CH:24]=[CH:23][S:22][C:21]=12)=[O:16]>CCCCCC>[N:9]1([CH2:8][C:4]2[CH:3]=[C:2]([CH:15]([OH:16])[C:17]3[N:18]=[CH:19][N:20]4[CH:24]=[CH:23][S:22][C:21]=34)[CH:7]=[N:6][CH:5]=2)[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1

Participants

4

Reactant 2

HCID 22390357Imidazo(4,3-b)(1,3)thiazole-7-carbaldehydeHCID 223904154-((5-Bromopyridin-3-yl)methyl)morpholine

Product 1

HCID 223901807-[[5-(Morpholin-4-yl)methylpyridin-3-yl]hydroxymethyl]imidazo[5,1-b]thiazoleYield 41.5%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

7-[[5-(Morpholin-4-yl)methylpyridin-3-yl]hydroxymethyl]imidazo[5,1-b]thiazole (384 mg) was prepared in substantially the same manner as in step a) of Synthesis Example 5, except that 1.05 g of 4-(5-bromopyridin-3-yl)methylmorpholine, 2.70 ml of a 1.59 N nbutyllithium/n-hexane solution, and 426 mg of 7-formylimidazo[5,1-b]thiazole were used as the starting materials.

Workup

  1. customof Synthesis Example 5

Sources & evidence

ORD record
ord-df5dc4982b4d4d7bab5afd77431c97f9
Source dataset
uspto-grants-2005_06
Patent number
US06908913B2

Reaction notes

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