N-bromobutanimide → HCID 90304142, compound

HRID 62446Notes

Reaction equation

HRID 62446 reaction equation
[Cl:1][C:2]1[C:3]2[N:4]([C:8]([CH:11]3[CH2:19][CH2:18][CH2:17][C:16]4[N:15]([CH3:20])[N:14]=[CH:13][C:12]3=4)=[N:9][CH:10]=2)[CH:5]=[CH:6][N:7]=1.C1C(=O)N([Br:28])C(=O)C1>CN(C=O)C>[Br:28][C:10]1[N:9]=[C:8]([CH:11]2[CH2:19][CH2:18][CH2:17][C:16]3[N:15]([CH3:20])[N:14]=[CH:13][C:12]2=3)[N:4]2[CH:5]=[CH:6][N:7]=[C:2]([Cl:1])[C:3]=12

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 903040078-chloro-3-(1-methyl-4,5,6,7-tetrahydro-1H-indazol-4-yl)imidazo[1,5-a]pyrazine

Product 1

HCID 90304142HCID 90304142, compoundYield 16%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 8-chloro-3-(1-methyl-4,5,6,7-tetrahydro-1H-indazol-4-yl)imidazo[1,5-a]pyrazine (1.0 g, 3.5 mmol) in DMF (20 mL) was added NBS (600 mg, 3.4 mmol) dropwise in DMF (20 mL) at 0° C. The mixture was stirred about 10 min under this condition, and then was poured into ice-water. The solid was filtered and dried under high vacuum to give 1-bromo-8-chloro-3-(1-methyl-4,5,6,7-tetrahydro-1H-indazol-4-yl)imidazo[1,5-a]pyrazine (200 mg, 15.6%). MS-ESI (m/z): 368 (M+1)+ (Acq Method: 10-80AB_2 min_220 &254.1 cm; Rt: 1.04 min)

Workup

  1. filtrationThe solid was filtered
  2. customdried under high vacuum

Sources & evidence

ORD record
ord-29c5ce9aba794e6faf4ea9d4fc6899ee
Source dataset
uspto-grants-2016_09
Patent number
US09446130B2

Reaction notes

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