Methanol → HCID 53230339, compound

HRID 1914911Notes

Reaction equation

HRID 1914911 reaction equation
[BH4-].[Na+].[F:3][C:4]1[C:9]2[CH:10]=[CH:11][O:12][C:8]=2[C:7]([NH:13][S:14]([C:17]2([CH2:20][CH:21]=[O:22])[CH2:19][CH2:18]2)(=[O:16])=[O:15])=[C:6]([NH:23][C:24]2[CH:29]=[CH:28][C:27]([I:30])=[CH:26][C:25]=2[F:31])[C:5]=1[F:32].CO.C(OCC)(=O)C>C1COCC1.CCCCCC>[F:3][C:4]1[C:9]2[CH:10]=[CH:11][O:12][C:8]=2[C:7]([NH:13][S:14]([C:17]2([CH2:20][CH2:21][OH:22])[CH2:19][CH2:18]2)(=[O:15])=[O:16])=[C:6]([NH:23][C:24]2[CH:29]=[CH:28][C:27]([I:30])=[CH:26][C:25]=2[F:31])[C:5]=1[F:32]

Participants

7

Reactant 4

HCID 887MethanolHCID 8857Ethyl AcetateHCID 4311764Sodium borohydrideHCID 86671490HCID 86671490, compound

Product 1

HCID 53230339HCID 53230339, compoundYield 46.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
10 °C

Procedure

NaBH4 (0.117 g, 0.82 mmol) was added to a solution of 1-(2-oxo-ethyl)-cyclopropanesulfonic acid [4,5-difluoro-6-(2-fluoro-4-iodo-phenylamino)-benzofuran-7-yl]-amide (0.086 g, 0.1557 mmol) in dry THF (10 mL) at 0° C. This was followed by the addition of methanol (2 mL) dropwise over a period of 10 minutes at 0° C. The reaction mass was stirred for 30 minutes at 10° C. The reaction was monitored by TLC (60% ethyl acetate in hexane). The reaction mass was partitioned between ethyl acetate (50 mL) and water. The organic layer was washed with water, brine solution and concentrated under reduced pressure to afford the crude product. Purification by column chromatography on silica gel (60% ethyl acetate in hexane) afforded 0.040 g of the product (46% yield). 1H NMR (DMSO-d6, 300 MHz): δ 9.56 (bs, 1H), 8.34 (d, 1H), 7.77 (bs, 1H), 7.56 (dd, 1H), 7.48 (d, 1H), 7.22 (d, 1H), 6.48-6.52 (m, 1H), 4.52 (bs, 1H), 3.51 (t, 2H), 2.20 (t, 2H), 0.85 (t, 2H), 0.55 (t, 2H). LCMS: 100%, m/z=550.8 (M−1). HPLC: 96.79%

Workup

  1. customThe reaction mass was partitioned between ethyl acetate (50 mL) and water
  2. washThe organic layer was washed with water, brine solution
  3. concentrationconcentrated under reduced pressure
  4. customto afford the crude product
  5. customPurification by column chromatography on silica gel (60% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-d1f1aba24c00482b8e4a2a87ba504e65
Source dataset
uspto-grants-2013_12
Patent number
US08614239B2

Reaction notes

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