Acetic Acid → HCID 25070630, compound

HRID 1715115Notes

Reaction equation

Cl.Cl.C([O:6][C:7]([C:9]1[CH:24]=[CH:23][C:12]2[N:13]([CH:17]3[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]3)[C:14]([CH3:16])=[N:15][C:11]=2[CH:10]=1)=[O:8])C=C.[OH-].[Na+].C(O)(=O)C.[CH2:31]([O:33][C:34]1[CH:35]=[C:36]([CH:39]=[CH:40][C:41]=1[F:42])[CH:37]=O)[CH3:32].C([BH3-])#N.[Na+]>CO.O.C(O)C>[CH2:31]([O:33][C:34]1[CH:35]=[C:36]([CH:39]=[CH:40][C:41]=1[F:42])[CH2:37][N:20]1[CH2:21][CH2:22][CH:17]([N:13]2[C:12]3[CH:23]=[CH:24][C:9]([C:7]([OH:8])=[O:6])=[CH:10][C:11]=3[N:15]=[C:14]2[CH3:16])[CH2:18][CH2:19]1)[CH3:32]

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of 2-methyl-1-piperidin-4-yl-1H-benzoimidazole-5-carboxylic acid allyl ester dihydrochloride (55.8 mg, 0.15 mmol, 1.0 equiv; intermediate A1) in methanol (0.8 mL) and water (0.4 mL) was added a solution of 10 M NaOH (60 μL), acetic acid (86 μL, 90.3 mg, 1.50 mmol, 10 equiv), 3-ethoxy-4-fluoro-benzaldehyde (30.3 mg, 0.18 mmol, 1.2 equiv; intermediate B1, vide infra) and sodium cyanoborohydride (47.1 mg, 0.75 mmol, 5.0 equiv), dissolved in ethanol (0.5 mL). The reaction mixture was stirred at 70° C. overnight. Removal of the solvent under reduced pressure and purification by preparative HPLC on reversed phase eluting with a gradient of acetonitrile/water provided 13.4 mg (22%) of the title compound. MS (ISP): 412.3 [M+H]+.

Workup

customRemoval of the solvent
customunder reduced pressure and purification by preparative HPLC on reversed phase
washeluting with a gradient of acetonitrile/water

Sources & evidence

ORD record: ord-0e4c0de59db9476bb6b58fad07721550
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07799806B2

Reaction notes

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