Sodium Hydroxide → HCID 10411682, compound

HRID 1991533Notes

Reaction equation

HRID 1991533 reaction equation
Cl.C([O:5][C@H:6]([CH2:21][NH:22][C:23]([C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([Br:32])[CH:27]=1)([CH3:25])[CH3:24])[C@@H:7]([NH:17][C:18](=[O:20])[CH3:19])[CH2:8][C:9]1[CH:14]=[C:13]([F:15])[CH:12]=[C:11]([F:16])[CH:10]=1)(=O)C.[OH-].[Na+]>CO>[Br:32][C:28]1[CH:27]=[C:26]([C:23]([NH:22][CH2:21][C@@H:6]([OH:5])[C@@H:7]([NH:17][C:18](=[O:20])[CH3:19])[CH2:8][C:9]2[CH:10]=[C:11]([F:16])[CH:12]=[C:13]([F:15])[CH:14]=2)([CH3:25])[CH3:24])[CH:31]=[CH:30][CH:29]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68537029HCID 68537029, compound

Product 1

HCID 10411682HCID 10411682, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 107 mg (0.21 mmol) of hydrochloride 31 in 10 mL of methanol is added 1 mL of 1N NaOH. The mixture is stirred for 45 min at ambient temperature, then quenched with 1N KH2PO4 and diluted with ethyl acetate. The organic phase is washed with brine, dried over Na2SO4, filtered and concentrated to a glassy solid. This is dissolved in methanol and treated with ethereal HCl to afford 70 mg (0.14 mmol, 68%) of compound 32 as a white solid: 1H NMR (CDCl3+CD3OD drop) δ 7.69 (s, 1H), 7.56 (m, 2H), 7.35 (t, J=8 Hz, 1H), 6.71 (m, 2H), 6.63 (m, 1H), 3.98 (m, 2H), 2.98 (m, 1H), 2.8 (m, 1H), 2.68 (m, 1H), 2.39 (m, 1H), 1.92 (s, 3H), 1.83 (s, 6H); IR (diffuse reflectance) 3311, 3283, 3257, 3249, 3058, 3007, 2757, 1655, 1646, 1628, 1596, 1551, 1459, 1116, 697 cm−1. MS (CI)m/z(rel intensity) 457 (15), 455 (MH+,97), 458 (17), 457 (99), 456 (15), 455 (97), 377 (5), 259 (9), 216 (6), 214 (6), 96 (27), 69 (5). HRMS (ESI) calcd for C21H25N2O2F2Br+H1 455.1146, found 455.1145. Anal. Calcd for C21H25BrF2N2O2.HCl+H2O: C, 49.47; H, 5.54; N, 5.49; Found: C, 49.45; H, 5.50; N, 5.54.

Workup

  1. customquenched with 1N KH2PO4
  2. additiondiluted with ethyl acetate
  3. washThe organic phase is washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated to a glassy solid
  7. dissolutionThis is dissolved in methanol
  8. additiontreated with ethereal HCl

Sources & evidence

ORD record
ord-bcd98cdaa9644dc98b16653748986862
Source dataset
uspto-grants-2010_01
Patent number
US07645780B2

Reaction notes

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