Chloroform → HCID 178527150, compound

HRID 1158639Notes

Reaction equation

HRID 1158639 reaction equation
[F:1][C:2]1[CH:30]=[CH:29][C:5]([CH2:6][C:7]2[NH:8][C:9]([C:12]3[C:21]([OH:22])=[C:20]4[C:15]([CH:16]=[CH:17][CH:18]=[N:19]4)=[C:14]([N:23]4[CH2:28][CH2:27]S[CH2:25][CH2:24]4)[N:13]=3)=[N:10][N:11]=2)=[CH:4][CH:3]=1.C(Cl)(Cl)Cl.O[O:36][S:37]([O-:39])=O.[K+]>CO>[O:36]=[S:37]1(=[O:39])[CH2:27][CH2:28][N:23]([C:14]2[N:13]=[C:12]([C:9]3[NH:8][C:7]([CH2:6][C:5]4[CH:4]=[CH:3][C:2]([F:1])=[CH:30][CH:29]=4)=[N:11][N:10]=3)[C:21]([OH:22])=[C:20]3[C:15]=2[CH:16]=[CH:17][CH:18]=[N:19]3)[CH2:24][CH2:25]1

Participants

5

Reactant 3

HCID 6212ChloroformHCID 23707502Potassium hydroxy sulfiteHCID 178515410HCID 178515410, compound

Product 1

HCID 178527150HCID 178527150, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A 100 mL flask was charged with 7-[5-(4-fluorobenzyl)-4H-1,2,4-triazol-3-yl]-5-thiomorpholin-4-yl-1,6-naphthyridin-8-ol (26 mg, 0.062 mmol). Methanol (15 mL) and chloroform (˜3 mL to dissolve insoluble solids) were added, followed by a freshly prepared 0.16 M solution of Oxone (0.75 mL, 0.12 mmol) in methanol. The solution was stirred for 14 hours at room temperature. The reaction mixture was concentrated in vacuo, diluted with dichloromethane and extracted twice. The combined organics were concentrated in vacuo and purified by preparative HPLC. Thus, 5-(1,1-dioxidothiomorpholin-4-yl)-7-[5-(4-fluorobenzyl)-4H-1,2,4-triazol-3-yl]-1,6-naphthyridin-8-ol (7.3 mg, 26%) was prepared as a tan solid. 1H NMR (CD3OD/CDCl3): δ 8.99 (dd, J=4.4, 1.6 Hz, 1 H), 8.31 (dd, J=8.4, 1.6 Hz, 1 H), 7.52 (dd, J=8.4, 4.4 Hz, 1 H), 7.24 (m, 2 H), 6.91 (m, 2 H), 4.08 (s, 2 H), 3.85 (m, 4 H), 3.25 (m, 4 H); MS m/z 455 (M+1).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additiondiluted with dichloromethane
  3. extractionextracted twice
  4. concentrationThe combined organics were concentrated in vacuo
  5. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-12458b5643ef44ea818ca4fa9b0d2931
Source dataset
uspto-grants-2010_10
Patent number
US07812016B2

Reaction notes

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