4-Methoxybenzylamine → (4-Methoxy-benzyl)-[3-(3-morpholin-4-ylmethyl-imidazo[2,1-b]thiazol-6-yl)-pyridin-2-yl]-amine

HRID 419876Notes

Reaction equation

HRID 419876 reaction equation
Cl[C:2]1[C:7]([C:8]2[N:9]=[C:10]3[N:14]([CH:15]=2)[C:13]([CH2:16][N:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)=[CH:12][S:11]3)=[CH:6][CH:5]=[CH:4][N:3]=1.BrC1C(C2N=C3N(C=2)C(CN2CCOCC2)=CS3)=CC=CN=1.[CH3:45][O:46][C:47]1[CH:54]=[CH:53][C:50]([CH2:51][NH2:52])=[CH:49][CH:48]=1>C1(C)C=CC=CC=1>[CH3:45][O:46][C:47]1[CH:54]=[CH:53][C:50]([CH2:51][NH:52][C:2]2[C:7]([C:8]3[N:9]=[C:10]4[N:14]([CH:15]=3)[C:13]([CH2:16][N:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)=[CH:12][S:11]4)=[CH:6][CH:5]=[CH:4][N:3]=2)=[CH:49][CH:48]=1

Participants

5

Reactant 3

HCID 754524-MethoxybenzylamineHCID 596799456-(2-Bromo-pyridin-3-yl)-3-morpholin-4-ylmethyl-imidazo[2,1-b]thiazoleHCID 596803366-(2-Chloro-pyridin-3-yl)-3-morpholin-4-ylmethyl-imidazo[2,1-b]thiazole

Product 1

HCID 59680069(4-Methoxy-benzyl)-[3-(3-morpholin-4-ylmethyl-imidazo[2,1-b]thiazol-6-yl)-pyridin-2-yl]-amine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The 1:1 mixture of 6-(2-Chloro-pyridin-3-yl)-3-morpholin-4-ylmethyl-imidazo [2,1-b]thiazole and 6-(2-bromo-pyridin-3-yl)-3-morpholin-4-ylmethyl-imidazo [2,1-b]thiazole (600 mg) was mixed with 15 mL of toluene along with 0.47 mL of 4-methoxybenzylamine and stirred under reflux for 5 days. The reaction mixture was cooled to room temperature and partitioned between CH2Cl2 and brine. The organic layer was separated, dried (Na2SO4) and concentrated to afford the crude product. Purification by chromatography (Isco, gradient elution, CH2Cl2 to 95% CH2Cl2, 4% MeOH and 1% Et3N) afforded 200 mg of (4-methoxy-benzyl)-[3-(3-morpholin -4-ylmethyl-imidazo[2,1-b]thiazol-6-yl)-pyridin-2-yl]-amine.

Workup

  1. temperatureunder reflux for 5 days
  2. custompartitioned between CH2Cl2 and brine
  3. customThe organic layer was separated
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customto afford the crude product
  7. customPurification
  8. washby chromatography (Isco, gradient elution, CH2Cl2 to 95% CH2Cl2, 4% MeOH and 1% Et3N)

Sources & evidence

ORD record
ord-ebdf33d09b734d798ba10745aeb2bf24
Source dataset
uspto-grants-2012_01
Patent number
US08093401B2

Reaction notes

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