Trityl chloride → 2-bromo-N-(1-methylcyclopropyl)-5-trityl-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide

HRID 246746Notes

Reaction equation

HRID 246746 reaction equation
[Br:1][C:2]1[N:7]=[C:6]2[C:8]([C:11]([NH:13][C:14]3([CH3:17])[CH2:16][CH2:15]3)=[O:12])=[CH:9][NH:10][C:5]2=[N:4][CH:3]=1.CCN(CC)CC.Cl[C:26]([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>C1COCC1>[Br:1][C:2]1[N:7]=[C:6]2[C:8]([C:11]([NH:13][C:14]3([CH3:17])[CH2:15][CH2:16]3)=[O:12])=[CH:9][N:10]([C:26]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)([C:39]3[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=3)[C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=3)[C:5]2=[N:4][CH:3]=1

Participants

5

Reactant 3

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 866780122-bromo-N-(1-methylcyclopropyl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide

Product 1

HCID 866780112-bromo-N-(1-methylcyclopropyl)-5-trityl-5H-pyrrolo[3,2-b]pyrazine-7-carboxamideYield 37%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 2-bromo-N-(1-methylcyclopropyl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide (600 mg, 2.1 mmol) in 20 mL of dry THF was added Et3N (0.42 mL, 4.2 mmol) and reaction mixture stirred for 5 mins, then (chloromethanetriyl)tribenzene (540 mg, 2.53 mmol) was added and reaction mixture stirred for 10 mins. Then, the reaction was heated to 60° C. and stirring continued for 3 hrs. The reaction was quenched with brine (10 mL), product extracted with ethyl acetate (3×20 mL), organics combined dried with sodium sulfate, filtered and concentrated to give 2-bromo-N-(1-methylcyclopropyl)-5-trityl-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide (400 mg, 37%) as yellow solid. 1H NMR (300 MHz, CDCl3): δ 8.32 (s, 1H), 8.01 (s, 1H), 7.31-7.26 (m, 15H), 1.51 (s, 3H), 1.25 (s, 2H), 0.90-0.74 (m, 2H). LCMS: (M+H)+=537/539.

Workup

  1. customreaction mixture
  2. stirringstirred for 10 mins
  3. stirringstirring
  4. waitcontinued for 3 hrs
  5. customThe reaction was quenched with brine (10 mL), product
  6. extractionextracted with ethyl acetate (3×20 mL)
  7. dry with materialorganics combined dried with sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-4c6021788fd64c4aa86872ea40b7f7e9
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

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