Water → HCID 178454636, compound

HRID 1508044Notes

Reaction equation

HRID 1508044 reaction equation
C[O:2][C:3](=[O:29])[C:4]([C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14]([C:16]2[NH:17][CH:18]=[C:19]([C:21]#[N:22])[N:20]=2)=[O:15])=[C:9]([C:23]2[CH2:28][CH2:27][CH2:26][CH2:25][CH:24]=2)[CH:8]=1)([CH3:6])[CH3:5].[OH-].[Na+].O>C1COCC1.CO>[C:21]([C:19]1[N:20]=[C:16]([C:14]([NH:13][C:10]2[CH:11]=[CH:12][C:7]([C:4]([CH3:6])([CH3:5])[C:3]([OH:29])=[O:2])=[CH:8][C:9]=2[C:23]2[CH2:28][CH2:27][CH2:26][CH2:25][CH:24]=2)=[O:15])[NH:17][CH:18]=1)#[N:22]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 178500102HCID 178500102, compound

Product 1

HCID 178454636HCID 178454636, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of 2-{4-[(4-cyano-1H-imidazole-2-carbonyl)-amino]-3-cyclohex-1-enyl-phenyl}-2-methyl-propionic acid methyl ester (as prepared in the previous step, 60.0 mg, 0.153 mmol) in 1 mL of 1:1 THF/MeOH was added 6 N NaOH (250 μL, 1.50 mmol). After stirring at RT for 18 h, the mixture was treated with 10 mL of H2O and washed with EtOAc (3×10 mL). The aqueous layer was acidified to a pH of 6 with 1 N aqueous HCl and extracted with 10:1 EtOAc-MeOH (3×10 mL). The combined organic layers were washed with H2O (10 mL), brine (10 mL) and dried (Na2SO4). The organic solvent was evaporated in vacuo to give the title compound (48 mg, 83%) as a white solid. 1H-NMR (CD3OD; 400 MHz): δ 8.19 (m, 1H), 7.90 (s, 1H), 7.31 (m, 1H), 7.20 (s, 1H), 5.84 (m, 1H), 2.17-2.40 (m, 4H), 1.76-1.92 (m, 4H), 1.57 (s, 6H). Mass spectrum (ESI, m/z): Calcd. for C21H22N4O3, 379.2 (M+H). found 379.2.

Workup

  1. washwashed with EtOAc (3×10 mL)
  2. extractionextracted with 10:1 EtOAc-MeOH (3×10 mL)
  3. washThe combined organic layers were washed with H2O (10 mL), brine (10 mL)
  4. dry with materialdried (Na2SO4)
  5. customThe organic solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-2f464b1313184481a562423813ec1c58
Source dataset
uspto-grants-2015_12
Patent number
US09221797B2

Reaction notes

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