Hydrochloric Acid → HCID 59558772, compound

HRID 1959087Notes

Reaction equation

HRID 1959087 reaction equation
[CH2:1]([NH2:3])[CH3:2].[F:4][C:5]1[C:31]([F:32])=[CH:30][CH:29]=[CH:28][C:6]=1[CH2:7][S:8][C:9]1[N:14]=[C:13]([NH:15][S:16]([N:19]2[CH2:24][CH2:23][C:22](=O)[CH2:21][CH2:20]2)(=[O:18])=[O:17])[CH:12]=[C:11]([O:26][CH3:27])[N:10]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+].Cl>C(Cl)Cl.C(O)(=O)C>[F:4][C:5]1[C:31]([F:32])=[CH:30][CH:29]=[CH:28][C:6]=1[CH2:7][S:8][C:9]1[N:14]=[C:13]([NH:15][S:16]([N:19]2[CH2:20][CH2:21][CH:22]([NH:3][CH2:1][CH3:2])[CH2:23][CH2:24]2)(=[O:17])=[O:18])[CH:12]=[C:11]([O:26][CH3:27])[N:10]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 6341EthylamineHCID 14798Sodium HydroxideHCID 5049666Sodium triacetoxyborohydrideHCID 67051257HCID 67051257, compound

Product 1

HCID 59558772HCID 59558772, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

Ethylamine (0.56 mL of 2M solution in methanol) was added to a solution of acetic acid (0.025 mL) and N-{2-[(2,3-difluorobenzyl)thio]-6-methoxypyrimidin-4-yl}-4-oxopiperidine-1-sulfonamide (the product of example 148, step iii) (0.10 g) in DCM (4 mL). The solution was stirred at room temperature for 1 h then sodium triacetoxyborohydride (0.24 g) was added in portions. The mixture was stirred at room temperature overnight then 3M aqueous sodium hydroxide (6 mL) added to the residue. The mixture was shaken vigorously then acidified to pH 8 with 2M aqueous hydrochloric acid and extracted with ethyl acetate. The combined organic extracts were concentrated then methanol (1 mL) was added and the resulting suspension filtered. The solid was washed with water, methanol and ethyl acetate to afford the title compound as a very pale yellow powder. Yield: 52 mg

Workup

  1. stirringThe mixture was stirred at room temperature overnight
  2. stirringThe mixture was shaken vigorously
  3. extractionextracted with ethyl acetate
  4. concentrationThe combined organic extracts were concentrated
  5. additionmethanol (1 mL) was added
  6. filtrationthe resulting suspension filtered
  7. washThe solid was washed with water, methanol and ethyl acetate

Sources & evidence

ORD record
ord-a887f13b3f24428da5ca8a801b89dd05
Source dataset
uspto-grants-2013_04
Patent number
US08410123B2

Reaction notes

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