Sodium Thiosulfate → 1-[2-(4-Cyclopentyloxy-6-methyl-5-{[methyl-(1,2,3,4-tetrahydro-naphthalen-1-yl)-amino]-methyl}-pyridin-2-yl)-6-fluoro-pheny]-propan-1-one

HRID 251653Notes

Reaction equation

HRID 251653 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[CH:23]1([O:28][C:29]2[C:34]([CH2:35][N:36]([CH3:47])[CH:37]3[C:46]4[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=4)[CH2:40][CH2:39][CH2:38]3)=[C:33]([CH3:48])[N:32]=[C:31]([C:49]3[CH:54]=[CH:53][CH:52]=[C:51]([F:55])[C:50]=3[CH:56]([OH:59])[CH2:57][CH3:58])[CH:30]=2)[CH2:27][CH2:26][CH2:25][CH2:24]1.[O-]S([O-])(=S)=O.[Na+].[Na+]>C(Cl)Cl>[CH:23]1([O:28][C:29]2[C:34]([CH2:35][N:36]([CH3:47])[CH:37]3[C:46]4[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=4)[CH2:40][CH2:39][CH2:38]3)=[C:33]([CH3:48])[N:32]=[C:31]([C:49]3[CH:54]=[CH:53][CH:52]=[C:51]([F:55])[C:50]=3[C:56](=[O:59])[CH2:57][CH3:58])[CH:30]=2)[CH2:27][CH2:26][CH2:25][CH2:24]1

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 596780542-(4-Cyclopentyloxy-6-methyl-5-{[methyl-(1,2,3,4-tetrahydro-naphthalen-1-yl)-amino]-methyl}-pyridin-2-yl)-6-fluoro-phenyl-propan-1-ol

Product 1

HCID 596781861-[2-(4-Cyclopentyloxy-6-methyl-5-{[methyl-(1,2,3,4-tetrahydro-naphthalen-1-yl)-amino]-methyl}-pyridin-2-yl)-6-fluoro-pheny]-propan-1-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dess-Martin reagent (170 mg, 0.4 mmol) is added to a solution of 1-[2-(4-cylopentyloxy-6-methyl-5-{[methyl-(1,2,3,4-tetrahydro-naphthalen-1-yl)-amino]-methyl}-pyridin-2-yl)-6-fluoro-pheny]-propan-1-ol (160 mg, 0.32 mmol) in DCM (4 mL) at room temperature and the resulting mixture is stirred for 2 hours, Saturated Na2S2O3 is added to the mixture and stirred for 10 minutes. The organic layer is separated and extracted with DCM (2×10 mL). The combined organic layers are dried and solvent is removed in vacuo to give 1-[2-(4-cylopentyloxy-6-methyl-5-{[methyl-(1,2,3,4-tetrahydro-naphthalen-1-yl)-amino]-methyl}-pyridin-2-yl)-6-fluoro-pheny]-propan-1-one which is used in the next step without further purification.

Workup

  1. stirringstirred for 10 minutes
  2. customThe organic layer is separated
  3. extractionextracted with DCM (2×10 mL)
  4. customThe combined organic layers are dried
  5. customsolvent is removed in vacuo

Sources & evidence

ORD record
ord-fe1d70d5c8f4468da1b3d4377582e707
Source dataset
uspto-grants-2011_01
Patent number
US07863454B2

Reaction notes

Loading…