Pyridine → HCID 11416753, compound

HRID 2099299Notes

Reaction equation

HRID 2099299 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([C:15]([OH:17])=O)[C:8]3[N:9]2[N:12]=[N:13][N:14]=3)=[CH:4][CH:3]=1.C(Cl)(C(Cl)=O)=O.N1C=CC=CC=1.[NH2:30][O:31][CH:32]1[CH2:37][CH2:36][CH2:35][CH2:34][O:33]1>C(Cl)Cl.CN(C=O)C>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([C:15]([NH:30][O:31][CH:32]3[CH2:37][CH2:36][CH2:35][CH2:34][O:33]3)=[O:17])[C:8]3[N:9]2[N:12]=[N:13][N:14]=3)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 1049PyridineHCID 65578Oxalyl chlorideHCID 5142091O-(Tetrahydropyran-2-yl)hydroxylamineHCID 59696618HCID 59696618, compound

Product 1

HCID 11416753HCID 11416753, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of carboxytetrazole (5, 0.05 g, 0.2 mmol) in CH2Cl2 (5 mL) at 0° C. under N2 was added DMF (4-drops) followed by (COCl)2 (IM CH2Cl2, 0.15 mL, 0.3 mmol) and the reaction was stirred for 1 h. The reaction solvent was removed and the resulting residue of acid chloride was dried under high vacuum. The acid chloride was then suspended in CH2Cl2 (5 mL), cooled to 0° C., to it was added pyridine (0.033 mL, 0.4 mmol) followed by H2N-OTHP (0.035 g, 0.3 mmol), and stirred at room temperature for 24 h. The CH2Cl2 solution was washed with water, dried and solvent was evaporated. The resulting residue was filtered through a pad of silica gel to obtain the requisite oxamic acid ester 6. 1H NMR (CDCl3): δ 11.58 (s, 1H), 8.92 (s, 1H), 8.74 (d, 1H, J=1.8 Hz), 8.10 (d, 1H, J=8.1 Hz), 7.77 (dd, 1H, J=1.8 Hz and 8.7 Hz), 5.26 (m, 1H), 4.15 (m, 1H), 3.76 (m, 1H), 2.10-1.50 (m, 6H); LCMS (ret. time): 21.46 min.; MS (m/z): 347 (MH+).

Workup

  1. customThe reaction solvent was removed
  2. dry with materialthe resulting residue of acid chloride was dried under high vacuum
  3. stirringstirred at room temperature for 24 h
  4. washThe CH2Cl2 solution was washed with water
  5. customdried
  6. customsolvent was evaporated
  7. filtrationThe resulting residue was filtered through a pad of silica gel

Sources & evidence

ORD record
ord-0bf29c6dd6204a3d8dcafd921c91c327
Source dataset
uspto-grants-2009_08
Patent number
US07569580B2

Reaction notes

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