Borane → HCID 54575204, compound

HRID 2190162Notes

Reaction equation

HRID 2190162 reaction equation
[CH3:1][NH:2][C:3]([C:5]1[C:13]2[C:8](=[N:9][C:10]([N:15]([CH2:20][CH2:21][CH2:22][C:23]#[N:24])[S:16]([CH3:19])(=[O:18])=[O:17])=[C:11]([I:14])[CH:12]=2)[O:7][C:6]=1[C:25]1[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=1)=[O:4].B>C1COCC1>[CH3:1][NH:2][C:3]([C:5]1[C:13]2[C:8](=[N:9][C:10]([N:15]([CH2:20][CH2:21][CH2:22][CH2:23][NH2:24])[S:16]([CH3:19])(=[O:18])=[O:17])=[C:11]([I:14])[CH:12]=2)[O:7][C:6]=1[C:25]1[CH:26]=[CH:27][C:28]([F:31])=[CH:29][CH:30]=1)=[O:4]

Participants

4

Reactant 2

HCID 6331BoraneHCID 54575200HCID 54575200, compound

Product 1

HCID 54575204HCID 54575204, compoundYield 44.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To the 6-[(3-Cyano-propyl)-methanesulfonyl-amino]-2-(4-fluoro-phenyl)-5-iodo-furo[2,3-b]pyridine-3-carboxylic acid methylamide (11 mg, 0.020 mmol) at 0° C. is added 0.5 mL 1N Borane in THF and stirred at 0° C. 5 min then stirred at room temperature overnight. The mixture is quenched with 1N HCl and THF is removed with a stream of N2. Purification is achieved by reverse phase HPLC with a C8 column with 10-50% ACN/H2O (0.1% NH4OH) to give 5 mg title compound. MS (ESI) m/z 561.0 (M+1). Retention time=1.00 min, Method A. 1H NMR (400 MHz, CD3CN) δ ppm 8.71 (s, 1H), 8.02-8.07 (m, 2H), 7.95 (t, 2H) 3.74 (t, 3H), 3.15 (s, 3H), 2.91 (d, 3H), 2.13-2.54 (m, 6H)

Workup

  1. stirring5 min then stirred at room temperature overnight
  2. customThe mixture is quenched with 1N HCl and THF
  3. customis removed with a stream of N2
  4. customPurification

Sources & evidence

ORD record
ord-2d5e6694ef57489faef65fc74782acd9
Source dataset
uspto-grants-2012_12
Patent number
US08324239B2

Reaction notes

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