Sodium Hydroxide → HCID 67025415, compound

HRID 1512870Notes

Reaction equation

HRID 1512870 reaction equation
[OH-].[Na+:2].[C:3]([C:5]1[CH:6]=[C:7]([C:15]2[O:19][N:18]=[C:17]([C:20]3[CH:21]=[C:22]4[C:26](=[CH:27][CH:28]=3)[NH:25][C:24](/[CH:29]=[CH:30]/[C:31]([O:33]CC)=[O:32])=[CH:23]4)[N:16]=2)[CH:8]=[CH:9][C:10]=1[O:11][CH:12]([CH3:14])[CH3:13])#[N:4]>C(O)C.O1CCOCC1>[C:3]([C:5]1[CH:6]=[C:7]([C:15]2[O:19][N:18]=[C:17]([C:20]3[CH:21]=[C:22]4[C:26](=[CH:27][CH:28]=3)[NH:25][C:24](/[CH:29]=[CH:30]/[C:31]([O-:33])=[O:32])=[CH:23]4)[N:16]=2)[CH:8]=[CH:9][C:10]=1[O:11][CH:12]([CH3:14])[CH3:13])#[N:4].[Na+:2]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 67094239HCID 67094239, compound

Product 1

HCID 67025415HCID 67025415, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 312751,4-DioxaneSolvent

Procedure

Aqueous NaOH solution (2 N, 2 mL) was added to a solution of ethyl (2E)-3-[5-(5-{3-cyano-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1H-indol-2-yl]-2-propenoate (D27) (20 mg) in ethanol (10 mL) and dioxane (5 mL) at RT. The resulting solution was stirred for 1 hour. Ethanol and dioxane were evaporated. The solid was filtered and washed with water. The solid was collected and dried to afford sodium (2E)-3-[5-(5-{3-cyano-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1H-indol-2-yl]-2-propenoate (E10) (8 mg) as a pale yellow solid. δH (DMSO-d6, 400 MHz): 1.39 (6H, d), 4.99 (1H, m), 6.48 (1H, d), 6.66 (1H, s), 7.11 (1H, d), 7.46 (1H, d), 7.56 (1H, d), 7.77 (1H, d), 8.25 (1H, s), 8.42 (1H, dd) 8.51 (1H, d). MS (ES): C25H21N4O4Na requires 436; found 415.0 (M—Na++2H+).

Workup

  1. customEthanol and dioxane were evaporated
  2. filtrationThe solid was filtered
  3. washwashed with water
  4. customThe solid was collected
  5. customdried

Sources & evidence

ORD record
ord-f989a92235bb4605a961b0bc1faa9bbf
Source dataset
uspto-grants-2012_07
Patent number
US08217028B2

Reaction notes

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