Bromopinacolone → HCID 178441350, compound

HRID 216376Notes

Reaction equation

HRID 216376 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([F:14])=[CH:10][N:9]=2)[CH:5]=[CH:4][C:3]=1[C:15]([OH:21])([CH3:20])[CH2:16][C:17](=[NH:19])[NH2:18].C(=O)(O)[O-].[K+].Br[CH2:28][C:29](=O)[C:30]([CH3:33])([CH3:32])[CH3:31]>O1CCCC1.O>[C:30]([C:29]1[N:19]=[C:17]([CH2:16][C:15]([C:3]2[CH:4]=[CH:5][C:6]([C:8]3[CH:13]=[CH:12][C:11]([F:14])=[CH:10][N:9]=3)=[CH:7][C:2]=2[F:1])([OH:21])[CH3:20])[NH:18][CH:28]=1)([CH3:33])([CH3:32])[CH3:31]

Participants

6

Reactant 3

HCID 21642BromopinacoloneHCID 516893Potassium BicarbonateHCID 68667785HCID 68667785, compound

Product 1

HCID 178441350HCID 178441350, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of the di(trifluoroacetate) salt of (±)-3-[2-fluoro-4-(5-fluoropyridin-2-yl)phenyl]-3-hydroxybutanimidamide (50 mg, 0.10 mmol), potassium bicarbonate (19 mg, 0.19 mmol) and 1-bromo-3,3-dimethylbutan-2-one (52 mg, 0.29 mmol) in tetrahydrofuran (1 mL) and water (0.25 mL) were stirred at ambient temperature overnight. Volatiles were removed in vacuo and the residue was purified by HPLC (Gilson; KR100-5C18 100×21.2 mm column; 10-100% MeCN/H2O) over 12 min to afford the title compound as a white solid. 1H NMR (500 MHz, CD3OD) δ 8.51 (d, J=2.8 Hz, 1H), 7.90 (dd, J=4.3, 8.8 Hz, 1H), 7.76-7.58 (m, 4H), 6.99 (s, 1H), 3.45 (AB, J=14.9 Hz, 2H), 3.30 (bs, 1H), 1.732 (s, 3H), 1.23 (s, 9H).

Workup

  1. customVolatiles were removed in vacuo
  2. customthe residue was purified by HPLC (Gilson; KR100-5C18 100×21.2 mm column; 10-100% MeCN/H2O) over 12 min

Sources & evidence

ORD record
ord-c48fb86908954c98a7c161c02c0088af
Source dataset
uspto-grants-2012_06
Patent number
US08193228B2

Reaction notes

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