Hydrochloric Acid → HCID 87546888, compound

HRID 1435697Notes

Reaction equation

HRID 1435697 reaction equation
[H-].[Na+].CS(O[CH2:8][CH2:9][C:10]1[N:11]=[C:12]([NH:15][S:16]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[C:20]=2[CH3:26])(=[O:18])=[O:17])[S:13][CH:14]=1)(=O)=[O:5].[NH:27]1[CH:31]=[CH:30][N:29]=[CH:28]1.Cl>C1COCC1.O>[OH2:5].[OH2:5].[Cl:25][C:21]1[C:20]([CH3:26])=[C:19]([S:16]([NH:15][C:12]2[S:13][CH:14]=[C:10]([CH2:9][CH2:8][N:27]3[CH:31]=[CH:30][N:29]=[CH:28]3)[N:11]=2)(=[O:17])=[O:18])[CH:24]=[CH:23][CH:22]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 795Imidazole2×HCID 24758Sodium hydride2×HCID 87545953HCID 87545953, compound

Product 1

HCID 87546888HCID 87546888, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

NaH (95% dry, 32 mg, 1.28 mmol) was added to a stirred solution of EXAMPLE 191A (250 mg, 0.61 mmol) and imidazole (46 mg, 0.67 mmol) in THF (10 mL) at room temperature. The mixture was stirred for 2 h at 40° C. when additional imidazole (41 mg, 0.61 mmol) and NaH (95% dry, 15 mg, 0.61 mmol) was added. The reaction was allowed to proceed for 1.5 h and was then neutralized by adding aqueous HCl (2 M). The solvent was evaporated and the resulting crude material was dissolved in TFA and purified by reversed phase flash chromatography on LiChroprep RP-18. The product was gradient eluting with (CH3CN in H2O/0.4% conc. HCl) to yield (80 mg, 0.21 mmol, 34%): MS (Ionspray, [M+H]+) m/z 382. Anal. Calcd. (found) for C15H15ClN4O2S2.2 H2O: C, 43.0 (42.9)%; H, 4.6 (4.3)%; N, 13.4 (13.7)%.

Workup

  1. additionwas added
  2. customThe solvent was evaporated
  3. dissolutionthe resulting crude material was dissolved in TFA
  4. custompurified by reversed phase flash chromatography on LiChroprep RP-18
  5. washThe product was gradient eluting with (CH3CN in H2O/0.4% conc. HCl)
  6. customto yield (80 mg, 0.21 mmol, 34%)

Sources & evidence

ORD record
ord-75a2e55e931645de92c6039d569c4593
Source dataset
uspto-grants-2009_11
Patent number
US07618961B2

Reaction notes

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