Hydrochloric Acid → HCID 59558799, compound

HRID 1025029Notes

Reaction equation

HRID 1025029 reaction equation
Cl.[NH:2]1[CH2:5][CH2:4][CH2:3]1.[F:6][C:7]1[C:33]([F:34])=[CH:32][CH:31]=[CH:30][C:8]=1[CH2:9][S:10][C:11]1[N:16]=[C:15]([NH:17][S:18]([N:21]2[CH2:26][CH2:25][C:24](=O)[CH2:23][CH2:22]2)(=[O:20])=[O:19])[CH:14]=[C:13]([O:28][CH3:29])[N:12]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+].Cl>C(Cl)Cl.C(O)(=O)C>[N:2]1([CH:24]2[CH2:25][CH2:26][N:21]([S:18]([NH:17][C:15]3[CH:14]=[C:13]([O:28][CH3:29])[N:12]=[C:11]([S:10][CH2:9][C:8]4[CH:30]=[CH:31][CH:32]=[C:33]([F:34])[C:7]=4[F:6])[N:16]=3)(=[O:19])=[O:20])[CH2:22][CH2:23]2)[CH2:5][CH2:4][CH2:3]1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 5049666Sodium triacetoxyborohydrideHCID 12308726Azetidine hydrochlorideHCID 67051257HCID 67051257, compound

Product 1

HCID 59558799HCID 59558799, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

Azetidine hydrochloride (0.11 g) 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 white powder. Yield: 47 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-1a921f7703a64bee9230d23aac2ad973
Source dataset
uspto-grants-2014_05
Patent number
US08722883B2

Reaction notes

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