Hydrochloric Acid → HCID 59558799, compound

HRID 2388902Notes

Reaction equation

HRID 2388902 reaction equation
Cl.N1CCC1.FC1C(F)=CC=CC=1CSC1N=C(NS(N2CCC(=O)CC2)(=O)=O)C=C(OC)N=1.[F:35][C:36]1[C:67]([F:68])=[CH:66][CH:65]=[CH:64][C:37]=1[CH2:38][S:39][C:40]1[N:45]=[C:44]([NH:46][S:47]([N:50]2[CH2:55][CH2:54][CH:53]([N:56]3[CH2:61][CH2:60]OC[CH2:57]3)[CH2:52][CH2:51]2)(=[O:49])=[O:48])[CH:43]=[C:42]([O:62][CH3:63])[N:41]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+].Cl>C(Cl)Cl.C(O)(=O)C>[N:56]1([CH:53]2[CH2:52][CH2:51][N:50]([S:47]([NH:46][C:44]3[CH:43]=[C:42]([O:62][CH3:63])[N:41]=[C:40]([S:39][CH2:38][C:37]4[CH:64]=[CH:65][CH:66]=[C:67]([F:68])[C:36]=4[F:35])[N:45]=3)(=[O:48])=[O:49])[CH2:55][CH2:54]2)[CH2:61][CH2:60][CH2:57]1

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 5049666Sodium triacetoxyborohydrideHCID 12308726Azetidine hydrochlorideHCID 53628422HCID 53628422, compoundHCID 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 (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 2 M 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-6b34f7a5ae524fc69f38d995c76d47d8
Source dataset
uspto-grants-2012_09
Patent number
US08269002B2

Reaction notes

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