Triethylamine → [2-(4-Chloro-2-methoxyphenyl)-4-methylthiazol-5-yl]carbamic acid 1,2,3,4-tetrahydrobenzo[4,5]imidazo[1,2-a]pyridin-7-ylmethyl ester

HRID 1498908Notes

Reaction equation

HRID 1498908 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][C:10](C(O)=O)=[C:11]([CH3:13])[N:12]=2)=[C:4]([O:17][CH3:18])[CH:3]=1.[CH2:19]1[N:24]2[C:25]3[CH:31]=[CH:30][C:29]([CH2:32][OH:33])=[CH:28][C:26]=3[N:27]=[C:23]2[CH2:22][CH2:21][CH2:20]1.C([N:36]([CH2:39]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:48])C=CC=CC=1>C1(C)C=CC=CC=1.C(Cl)(Cl)Cl>[CH2:19]1[N:24]2[C:25]3[CH:31]=[CH:30][C:29]([CH2:32][O:33][C:39](=[O:48])[NH:36][C:10]4[S:9][C:8]([C:5]5[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][C:4]=5[O:17][CH3:18])=[N:12][C:11]=4[CH3:13])=[CH:28][C:26]=3[N:27]=[C:23]2[CH2:22][CH2:21][CH2:20]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 56598510(1,2,3,4-Tetrahydrobenzo[4,5]imidazo[1,2-a]pyridine-7-yl)methanolHCID 686420482-(4-Chloro-2-methoxyphenyl)-4-methylthiazole-5-carboxylic acid

Product 1

HCID 86679342[2-(4-Chloro-2-methoxyphenyl)-4-methylthiazol-5-yl]carbamic acid 1,2,3,4-tetrahydrobenzo[4,5]imidazo[1,2-a]pyridin-7-ylmethyl esterYield 71%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6212ChloroformSolvent

Procedure

In toluene (50 ml), 2-(4-chloro-2-methoxyphenyl)-4-methylthiazole-5-carboxylic acid (1.11 g, 3.91 mmol) prepared in Example 7-1 and (1,2,3,4-tetrahydrobenzo[4,5]imidazo[1,2-a]pyridin-7-yl)methanol (870 mg, 4.30 mmol) prepared in Example 3-1 were suspended. Triethylamine (475 mg, 4.69 mmol) and then diphenylphosphoryl azide (1.18 g, 4.30 mmol) were added to the suspension, and the mixture was heated under reflux for 2 hours. Chloroform was added to the mixture, and the resulting mixture was washed with a saturated sodium bicarbonate solution. The washed mixture was dried over anhydrous magnesium sulfate and then concentrated. The concentrate was purified by silica gel column chromatography (chloroform:methanol=10:1) to give the title compound (1.34 g, 71%) as a white powder.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2 hours
  3. washthe resulting mixture was washed with a saturated sodium bicarbonate solution
  4. dry with materialThe washed mixture was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customThe concentrate was purified by silica gel column chromatography (chloroform:methanol=10:1)

Sources & evidence

ORD record
ord-5372ac7d071c426e9ea972d81a41c685
Source dataset
uspto-grants-2015_12
Patent number
US09200008B2

Reaction notes

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