N-bromobutanimide → HCID 66897087, compound

HRID 1913243Notes

Reaction equation

HRID 1913243 reaction equation
[CH3:1][Si:2]([CH3:51])([CH3:50])[CH2:3][CH2:4][O:5][CH2:6][N:7]([CH2:42][O:43][CH2:44][CH2:45][Si:46]([CH3:49])([CH3:48])[CH3:47])[C:8]1[N:13]2[N:14]=[CH:15][C:16]([C:17]3[CH:18]=[N:19][C:20]4[C:25]([CH:26]=3)=[CH:24][CH:23]=[CH:22][CH:21]=4)=[C:12]2[N:11]=[C:10]([CH2:27][N:28]([CH:36]2[CH2:41][CH2:40][O:39][CH2:38][CH2:37]2)[C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:33])[CH3:32])[CH:9]=1.[Br:52]N1C(=O)CCC1=O>CC#N>[CH3:49][Si:46]([CH3:48])([CH3:47])[CH2:45][CH2:44][O:43][CH2:42][N:7]([CH2:6][O:5][CH2:4][CH2:3][Si:2]([CH3:1])([CH3:50])[CH3:51])[C:8]1[N:13]2[N:14]=[CH:15][C:16]([C:17]3[CH:18]=[N:19][C:20]4[C:25]([CH:26]=3)=[CH:24][CH:23]=[CH:22][CH:21]=4)=[C:12]2[N:11]=[C:10]([CH2:27][N:28]([CH:36]2[CH2:41][CH2:40][O:39][CH2:38][CH2:37]2)[C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:33])[CH3:32])[C:9]=1[Br:52]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 66881223HCID 66881223, compound

Product 1

HCID 66897087HCID 66897087, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To crude tert-butyl (7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-3-(quinolin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)methyl(tetrahydro-2H-pyran-4-yl)carbamate (Int-8d, 44 mg) in CH3CN (8 mL) was added N-bromosuccinimide (22 mg, 0.12 mmol), followed by additional CH3CN (4 mL). The reaction was then stirred at room temperature for 30 minutes, at which time LC/MS analysis confirmed full conversion of the starting material to the product. The reaction mixture was concentrated in vacuo and purified by preparative HPLC to give Int-8e as a yellow solid (8.7 mg, 0.02 mmol, 7% over three steps). LCMS: 0.82 mins, m/z=812.10 and 813.20 (MH+).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. custompurified by preparative HPLC
  3. customto give Int-8e as a yellow solid (8.7 mg, 0.02 mmol, 7% over three steps)
  4. custom0.82 mins, m/z=812.10 and 813.20 (MH+)

Sources & evidence

ORD record
ord-6b57abe192ec43918a1e98d953306119
Source dataset
uspto-grants-2013_12
Patent number
US08609675B2

Reaction notes

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