N-bromobutanimide → HCID 86686742, compound

HRID 2369021Notes

Reaction equation

HRID 2369021 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][C:23]([F:27])=[CH:22][CH:21]=4)=[C:12]2[N:11]=[C:10]([CH:28]([NH:30][C:31]([C:33]2([CH3:41])[CH2:38][O:37][C:36]([CH3:40])([CH3:39])[O:35][CH2:34]2)=[O:32])[CH3:29])[CH:9]=1.[Br:52]N1C(=O)CCC1=O>C(O)(=O)C>[CH3:51][Si:2]([CH3:1])([CH3:50])[CH2:3][CH2:4][O:5][CH2:6][N:7]([CH2:42][O:43][CH2:44][CH2:45][Si:46]([CH3:47])([CH3:48])[CH3:49])[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][C:23]([F:27])=[CH:22][CH:21]=4)=[C:12]2[N:11]=[C:10]([CH:28]([NH:30][C:31]([C:33]2([CH3:41])[CH2:38][O:37][C:36]([CH3:40])([CH3:39])[O:35][CH2:34]2)=[O:32])[CH3:29])[C:9]=1[Br:52]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 86686743HCID 86686743, compound

Product 1

HCID 86686742HCID 86686742, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

N-{1-[7-(bis{[2-(trimethylsilyl)ethoxy]methyl}amino)-3-(6-fluoroquinolin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl]ethyl}-2,2,5-trimethyl-1,3-dioxane-5-carboxamide (370 mg, 0.501 mmol) was dissolved in acetic acid (13 mL). and N-bromosuccinimide (104 mg, 0.585 mmol) was added in a single portion, and the reaction was stirred for 10 min before being quenched with 20% aq. Na2S2O3 (20 mL) and saturated aq. NaHCO3 (60 mL) and EtOAc (50 mL). Solid NaHCO3 was added until the pH was above 5. The layers were separated, and the aqueous was extracted with EtOAc (2×50 mL). The combined organics were washed with brine (50 mL), dried with MgSO4, filtered, and concentrated in vacuo to give N-{1-[7-(bis{[2-(trimethylsilyl)ethoxy]methyl}amino)-6-bromo-3-(6-fluoroquinolin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl]ethyl}-2,2,5-trimethyl-1,3-dioxane-5-carboxamide, which was used without further purification.

Workup

  1. custombefore being quenched with 20% aq. Na2S2O3 (20 mL) and saturated aq. NaHCO3 (60 mL) and EtOAc (50 mL)
  2. additionSolid NaHCO3 was added until the pH was above 5
  3. customThe layers were separated
  4. extractionthe aqueous was extracted with EtOAc (2×50 mL)
  5. washThe combined organics were washed with brine (50 mL)
  6. dry with materialdried with MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3ad3c4e914584a04b9aae8dc1f65a969
Source dataset
uspto-grants-2014_04
Patent number
US08703784B2

Reaction notes

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