Tetrahydrofuran → HCID 59026827, compound

HRID 658383Notes

Reaction equation

HRID 658383 reaction equation
C[O:2][C:3](=O)[CH2:4][NH:5][C:6]1[O:7][C:8]([C:11]2[CH:16]=[CH:15][N:14]=[CH:13][C:12]=2[NH:17][C:18]2[CH:23]=[CH:22][C:21]([I:24])=[CH:20][C:19]=2[F:25])=[N:9][N:10]=1.C1COCC1>>[F:25][C:19]1[CH:20]=[C:21]([I:24])[CH:22]=[CH:23][C:18]=1[NH:17][C:12]1[CH:13]=[N:14][CH:15]=[CH:16][C:11]=1[C:8]1[O:7][C:6]([NH:5][CH2:4][CH2:3][OH:2])=[N:10][N:9]=1

Participants

3

Reactant 2

HCID 8028TetrahydrofuranHCID 59026775HCID 59026775, compound

Product 1

HCID 59026827HCID 59026827, compoundYield 50.7%

Procedure

To a solution of {5-[3-(2-Fluoro-4-iodo-phenylamino)-pyridin-4-yl]-[1,3,4]oxadiazol-2-ylamino}-acetic acid methyl ester (400 mg, 0.85 mmol, 1 eq) in THF (5 mL) LiBH4 (37 mg, 1.7 mmol, 2 eq) was added. The reaction mixture was stirred at RT for 20 hrs and then quenched with methanol and then added water. The solvent was partially removed and EtOAc was added. A solid precipitated out that was filtered to give the desired product (190 mg). LC/MS (Method A) [4.48 min; 442(M+1)]

Workup

  1. customquenched with methanol
  2. customThe solvent was partially removed
  3. additionEtOAc was added
  4. customA solid precipitated out
  5. filtrationthat was filtered

Sources & evidence

ORD record
ord-4061fd5b47b344bb805bd8293a28da87
Source dataset
uspto-grants-2011_12
Patent number
US08076486B2

Reaction notes

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