N-bromobutanimide → HCID 67494315, compound

HRID 2047041Notes

Reaction equation

HRID 2047041 reaction equation
[CH3:1][S:2]([C:5]1[CH:47]=[CH:46][C:8]([O:9][C:10]2[CH:15]=[C:14]([N:16]([CH2:25][O:26][CH2:27][CH2:28][Si:29]([CH3:32])([CH3:31])[CH3:30])[CH2:17][O:18][CH2:19][CH2:20][Si:21]([CH3:24])([CH3:23])[CH3:22])[N:13]3[N:33]=[CH:34][C:35]([C:36]4[CH:37]=[N:38][C:39]5[C:44]([CH:45]=4)=[CH:43][CH:42]=[CH:41][CH:40]=5)=[C:12]3[N:11]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].C1C(=O)N([Br:55])C(=O)C1>C(#N)C>[Br:55][C:15]1[C:10]([O:9][C:8]2[CH:46]=[CH:47][C:5]([S:2]([CH3:1])(=[O:3])=[O:4])=[CH:6][CH:7]=2)=[N:11][C:12]2[N:13]([N:33]=[CH:34][C:35]=2[C:36]2[CH:37]=[N:38][C:39]3[C:44]([CH:45]=2)=[CH:43][CH:42]=[CH:41][CH:40]=3)[C:14]=1[N:16]([CH2:25][O:26][CH2:27][CH2:28][Si:29]([CH3:32])([CH3:31])[CH3:30])[CH2:17][O:18][CH2:19][CH2:20][Si:21]([CH3:22])([CH3:23])[CH3:24]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 66735928HCID 66735928, compound

Product 1

HCID 67494315HCID 67494315, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Compound, 5-(4-(methylsulfonyl)phenoxy)-3-(quinolin-3-yl)-N,N-bis((2-(trimethylsilyl)ethoxy)methyl)pyrazolo[1,5-a]pyrimidin-7-amine (150 mg, 0.22 mmol) was dissolved in ACN (10 mL). NBS (40 mg, 0.22 mmol) was added and the mixture was stirred at room temperature for 1 h. After concentration, the residue, 6-bromo-5-(4-(methylsulfonyl)phenoxy)-3-(quinolin-3-yl)-N,N-bis((2-(trimethylsilyl)ethoxy)methyl)pyrazolo[1,5-a]pyrimidin-7-amine was used in the next step without further purification. HPLC-MS tR=2.66 min (UV254 nm); mass calculated for formula C34H44BrN5O5SSi2 769.2, observed LCMS m/z 770.0 (M+H).

Workup

  1. concentrationAfter concentration
  2. customthe residue, 6-bromo-5-(4-(methylsulfonyl)phenoxy)-3-(quinolin-3-yl)-N,N-bis((2-(trimethylsilyl)ethoxy)methyl)pyrazolo[1,5-a]pyrimidin-7-amine was used in the next step without further purification

Sources & evidence

ORD record
ord-65312ddc1391415f9f9282f21538ad64
Source dataset
uspto-grants-2013_11
Patent number
US08591943B2

Reaction notes

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