(Methylthio)acetic acid → HCID 54766757, compound

HRID 2045950Notes

Reaction equation

HRID 2045950 reaction equation
[CH3:1][S:2][CH2:3][C:4]([OH:6])=O.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[Cl:49][C:50]1[CH:51]=[C:52]([C:57]2([C:70]([F:73])([F:72])[F:71])[O:61][N:60]=[C:59]([C:62]3[S:66][C:65]([CH2:67][NH2:68])=[C:64]([CH3:69])[CH:63]=3)[CH2:58]2)[CH:53]=[C:54]([Cl:56])[CH:55]=1>ClCCl>[Cl:49][C:50]1[CH:51]=[C:52]([C:57]2([C:70]([F:71])([F:73])[F:72])[O:61][N:60]=[C:59]([C:62]3[S:66][C:65]([CH2:67][NH:68][C:4](=[O:6])[CH2:3][S:2][CH3:1])=[C:64]([CH3:69])[CH:63]=3)[CH2:58]2)[CH:53]=[C:54]([Cl:56])[CH:55]=1

Participants

6

Reactant 4

HCID 75551(Methylthio)acetic acidHCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 66587222HCID 66587222, compound

Product 1

HCID 54766757HCID 54766757, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(Methylthio)acetic acid (29 μl), PyBOP (126 mg) and Hünig base (115 μl) is added to a solution of C-{5-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-3-methyl-thiophen-2-yl}-methylamine (90 mg) in dichloromethane (2 ml). After 1 hour at room temperature, the reaction is quenched with water. The reaction mixture is extracted three times with dichloromethane. The combined organic phases are extracted with a saturated solution of NaHCO3 and with a saturated aqueous solution of NaCl, dried over Na2SO4 and concentrated in vacuo. The crude product is purified on a semi-preparative HPLC to yield N-{5-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-3-methyl-thiophen-2-ylmethyl}-2-methylsulfanyl-acetamide (82 mg, compound 1.10 in Table 1) as a white foam. MS (HPLC/MS): 497 (MH+). Retention time: 2.00 min.

Workup

  1. customthe reaction is quenched with water
  2. extractionThe reaction mixture is extracted three times with dichloromethane
  3. extractionThe combined organic phases are extracted with a saturated solution of NaHCO3 and with a saturated aqueous solution of NaCl
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe crude product is purified on a semi-preparative HPLC

Sources & evidence

ORD record
ord-ef0da886472b43a4a84c0e8bccdf10cc
Source dataset
uspto-grants-2013_11
Patent number
US08592418B2

Reaction notes

Loading…