Water → HCID 56962847, compound

HRID 1037555Notes

Reaction equation

HRID 1037555 reaction equation
[Si]([O:8][CH2:9][CH2:10][N:11]([S:34]([CH3:37])(=[O:36])=[O:35])[C:12]1[C:13]([O:32][CH3:33])=[CH:14][C:15]2[C:19]([CH:20]=1)=[N:18][N:17]([C:21]1[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=1)[C:16]=2[C:28]([NH:30][CH3:31])=[O:29])(C(C)(C)C)(C)C.[F-].[NH4+].O>CO>[F:27][C:24]1[CH:25]=[CH:26][C:21]([N:17]2[C:16]([C:28]([NH:30][CH3:31])=[O:29])=[C:15]3[C:19]([CH:20]=[C:12]([N:11]([CH2:10][CH2:9][OH:8])[S:34]([CH3:37])(=[O:35])=[O:36])[C:13]([O:32][CH3:33])=[CH:14]3)=[N:18]2)=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 962WaterHCID 25516Ammonium fluorideHCID 67776003HCID 67776003, compound

Product 1

HCID 56962847HCID 56962847, compoundYield 33.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of Compound (11) (250 mg, 0.45 mmol) in MeOH (20 mL) was added ammonium fluoride (166 mg, 4.5 mmol) and water (5 mL). The reaction mixture was heated to 60° C. for 5 h (monitored by TLC and LCMS). MeOH was removed in vacuo and the residue was diluted with water. The resulting precipitate was filtered, washed with ethanol and dried in vacuo at 40° C. to give Compound (12) (65 mg, 33%). ESI-MS m/z calculated for [M+Na]+: 459.11; found: 459.11; 1H NMR (400 MHz, d6-DMSO) δ 8.65 (s, 1H), 7.77 (s, 1H), 7.65-7.52 (m, 2H), 7.46-7.32 (m, 2H), 7.15 (s, 1H), 4.80-4.70 (m, 1H), 3.92 (s, 3H), 3.78-3.39 (m, 4H), 3.08 (s, 3H), 2.88-2.77 (m, 3H).

Workup

  1. customMeOH was removed in vacuo
  2. additionthe residue was diluted with water
  3. filtrationThe resulting precipitate was filtered
  4. washwashed with ethanol
  5. customdried in vacuo at 40° C.

Sources & evidence

ORD record
ord-2c91d0b2a32b4e0b8ee6b2d2e63688f0
Source dataset
uspto-grants-2013_10
Patent number
US08546389B2

Reaction notes

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