Acetic Acid → HCID 89583164, compound

HRID 402838Notes

Reaction equation

HRID 402838 reaction equation
Cl.[O:2]=[C:3]1[N:7]([C:8]2[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[CH:10][CH:9]=2)[CH2:6][C:5]2([CH2:22][CH2:21][NH:20][CH2:19][CH2:18]2)[O:4]1.[Cl:23][C:24]1[CH:29]=[C:28]([CH:30]=O)[CH:27]=[C:26]([Cl:32])[C:25]=1[C:33]1[CH:38]=[CH:37][C:36]([F:39])=[CH:35][CH:34]=1.C(O)(=O)C.C([BH3-])#N>ClCCCl.CO>[Cl:23][C:24]1[C:25]([C:33]2[CH:38]=[CH:37][C:36]([F:39])=[CH:35][CH:34]=2)=[C:26]([Cl:32])[CH:27]=[C:28]([CH2:30][N:20]2[CH2:21][CH2:22][C:5]3([O:4][C:3](=[O:2])[N:7]([C:8]4[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[CH:10][CH:9]=4)[CH2:6]3)[CH2:18][CH2:19]2)[CH:29]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 498716Cyano-borohydrideHCID 66764605Methyl 4-(2-oxo-1-oxa-3,8-diazaspiro[4.5]dec-3-yl)benzoate hydrochloride saltHCID 86676810HCID 86676810, compound

Product 1

HCID 89583164HCID 89583164, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 887MethanolSolvent

Procedure

To a solution of methyl 4-(2-oxo-1-oxa-3,8-diazaspiro[4.5]dec-3-yl)benzoate (27 mg, 0.084 mmol) (from Example 1-1, Step 2) and 2,6-dichloro-4′-fluorobiphenyl-4-carboxaldehyde (15 mg, 0.056 mmol) (from Step 3) in DCE (2 mL) and methanol (2 mL) in a 20 mL scintillation vial was added acetic acid (10 uL, 0.168 mmol) and MP-cyanoborohydride resin (56 mg, 0.140 mmol, 2.49 mmol/g). The mixture was shaken at room temperature for 18 hours and was then filtered to remove the resin. The volatiles were removed in vacuo and the residue was used directly in Step 5

Workup

  1. filtrationwas then filtered
  2. customto remove the resin
  3. customThe volatiles were removed in vacuo

Sources & evidence

ORD record
ord-c88256f040644d10bc0a93fade3455a2
Source dataset
uspto-grants-2014_06
Patent number
US08742110B2

Reaction notes

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