Toluene → methyl 5-(N-(5-cyclopropyl-3-(methylcarbamoyl)-2-p-tolylfuro[2,3-b]pyridin-6-yl)methylsulfonamido)pentanoate

HRID 2190169Notes

Reaction equation

HRID 2190169 reaction equation
I[C:2]1[CH:3]=[C:4]2[C:23]([C:24](=[O:27])[NH:25][CH3:26])=[C:22]([C:28]3[CH:33]=[CH:32][C:31]([CH3:34])=[CH:30][CH:29]=3)[O:21][C:5]2=[N:6][C:7]=1[N:8]([CH2:13][CH2:14][CH2:15][CH2:16][C:17]([O:19][CH3:20])=[O:18])[S:9]([CH3:12])(=[O:11])=[O:10].[C:35]1([CH3:41])C=CC=C[CH:36]=1>>[CH:41]1([C:2]2[CH:3]=[C:4]3[C:23]([C:24](=[O:27])[NH:25][CH3:26])=[C:22]([C:28]4[CH:29]=[CH:30][C:31]([CH3:34])=[CH:32][CH:33]=4)[O:21][C:5]3=[N:6][C:7]=2[N:8]([CH2:13][CH2:14][CH2:15][CH2:16][C:17]([O:19][CH3:20])=[O:18])[S:9]([CH3:12])(=[O:11])=[O:10])[CH2:35][CH2:36]1

Participants

3

Reactant 2

HCID 1140TolueneHCID 58052375methyl 5-(N-(5-iodo-3-(methylcarbamoyl)-2-p-tolylfuro[2,3-b]pyridin-6-yl)methylsulfonamido)pentanoate

Product 1

HCID 58052537methyl 5-(N-(5-cyclopropyl-3-(methylcarbamoyl)-2-p-tolylfuro[2,3-b]pyridin-6-yl)methylsulfonamido)pentanoateYield 67%

Procedure

The methyl 5-(N-(5-iodo-3-(methylcarbamoyl)-2-p-tolylfuro[2,3-b]pyridin-6-yl)methylsulfonamido)pentanoate (35 mg, 0.058 mmol) was suspended/dissolved in 1 mL toluene and added to 2. 1 was added to 2. The biphasic mixture was degassed for 5 min, then microwaved at 122° C. for 10 min. The mixture was then heated again at the same temperature for another 2×10 min. HPLC purification yielded methyl 5-(N-(5-cyclopropyl-3-(methylcarbamoyl)-2-p-tolylfuro[2,3-b]pyridin-6-yl)methylsulfonamido)pentanoate (20 mg, 0.039 mmol, 67%) MS-ES [M+H]+=513.9, LC RT=1.60 min, Method A.

Workup

  1. additionadded to 2
  2. addition1 was added to 2
  3. customThe biphasic mixture was degassed for 5 min
  4. custommicrowaved at 122° C. for 10 min
  5. temperatureThe mixture was then heated again at the same temperature for another 2×10 min
  6. customHPLC purification

Sources & evidence

ORD record
ord-d7292639f7114da4a8ace1be88444d91
Source dataset
uspto-grants-2012_12
Patent number
US08324239B2

Reaction notes

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