N-bromobutanimide → HCID 58382511, compound

HRID 1628087Notes

Reaction equation

HRID 1628087 reaction equation
[S:1]([N:11]1[C:15]2[N:16]=[CH:17][C:18]3[N:19]([CH:20]=[N:21][C:22]=3[C:23]3[CH:28]=[CH:27][C:26]([C:29]([OH:32])([CH3:31])[CH3:30])=[CH:25][CH:24]=3)[C:14]=2[CH:13]=[CH:12]1)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].C1C(=O)N([Br:40])C(=O)C1>CN(C=O)C.O>[Br:40][C:20]1[N:19]2[C:14]3[CH:13]=[CH:12][N:11]([S:1]([C:4]4[CH:5]=[CH:6][C:7]([CH3:8])=[CH:9][CH:10]=4)(=[O:2])=[O:3])[C:15]=3[N:16]=[CH:17][C:18]2=[C:22]([C:23]2[CH:28]=[CH:27][C:26]([C:29]([OH:32])([CH3:30])[CH3:31])=[CH:25][CH:24]=2)[N:21]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 58382426HCID 58382426, compound

Product 1

HCID 58382511HCID 58382511, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

2-(4-(6-Tosyl-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazin-3-yl)phenyl)propan-2-ol (0.285 g, 0.638 mmol, prepared using J.3 from Example #2, Step B with ethyl formate, L.2 with POCl3, AB and D with Preparation #H.1) was dissolved in DMF (3 mL) then treated with NBS (0.114 g, 0.638 mmol). The mixture was stirred for about 15 min then diluted with water (20 mL). The solid was collected by filtration then washed with water (5 mL). The material was dried under vacuum at about 70° C. to a constant weight to give 2-(4-(1-bromo-6-tosyl-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazin-3-yl)phenyl)propan-2-ol (0.285 g, 85%): LC/MS (Table 2, Method b) Rt=2.58 min; MS m/z 527 (M+H)+.

Workup

  1. filtrationThe solid was collected by filtration
  2. washthen washed with water (5 mL)
  3. customThe material was dried under vacuum at about 70° C. to a constant weight

Sources & evidence

ORD record
ord-e736c69783884a2c9d80767e234ef986
Source dataset
uspto-grants-2014_07
Patent number
US08785639B2

Reaction notes

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