Borane → HCID 59464071, compound

HRID 1713733Notes

Reaction equation

HRID 1713733 reaction equation
B.[F:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9][C:10]1[O:14][C:13]([C:15]([NH:17][C:18]2[CH:23]=[CH:22][C:21]([CH:24]3[CH2:29][CH2:28][CH:27]([CH2:30][C:31](O)=[O:32])[CH2:26][CH2:25]3)=[CH:20][CH:19]=2)=[O:16])=[N:12][N:11]=1>C1COCC1>[F:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9][C:10]1[O:14][C:13]([C:15]([NH:17][C:18]2[CH:19]=[CH:20][C:21]([CH:24]3[CH2:29][CH2:28][CH:27]([CH2:30][CH2:31][OH:32])[CH2:26][CH2:25]3)=[CH:22][CH:23]=2)=[O:16])=[N:12][N:11]=1

Participants

4

Reactant 2

HCID 6331BoraneHCID 59464331HCID 59464331, compound2×

Product 1

HCID 59464071HCID 59464071, compoundYield 45.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Borane (1 mL of a 1M solution in THF) was added to a stirred solution of (4-{4-[({5-[(2-fluorophenyl)amino]-1,3,4-oxadiazol-2-yl}carbonyl)amino]phenyl}cyclohexyl)acetic acid (Intermediate 45, 79 mg) in THF (2 mL). The reaction mixture was stirred for 16 hours. The mixture was evaporated and the residue dissolved in DCM (10 mL) then washed with brine (10 mL), dried and concentrated in vacuo to give a solid. This solid was purified by HPLC eluting with a gradient of acetonitrile/water containing 0.2% TFA to give the title compound (35 mg) as a solid, a ca. 2:1 trans:cis isomeric mixture; 1H NMR δ 10.90 (1H, s), 10.72 (1H, s), 8.01 (1H, t), 7.65 (2H, m), 7.33-7.12 (5H, m), 4.28 (1H, m), 3.46 (2H, bs), 2.58-2.40 (1H+ DMSO, m), 1.80 (3H, bs), 1.68-1.50 (4H, m), 1.49-1.31 (3H, m), 1.05 (1H, m); MS m/e MH+ 425.

Workup

  1. customThe mixture was evaporated
  2. dissolutionthe residue dissolved in DCM (10 mL)
  3. washthen washed with brine (10 mL)
  4. customdried
  5. concentrationconcentrated in vacuo
  6. customto give a solid
  7. customThis solid was purified by HPLC
  8. washeluting with a gradient of acetonitrile/water containing 0.2% TFA

Sources & evidence

ORD record
ord-2c754996e0b842ba902b037c6439fb18
Source dataset
uspto-grants-2010_09
Patent number
US07795283B2

Reaction notes

Loading…