Hydrochloric Acid → HCID 86600986, compound

HRID 2221167Notes

Reaction equation

HRID 2221167 reaction equation
CO[C:3](=[O:36])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][CH2:12][N:13]([C:27]2[O:31]C3C=CC=CC=3[CH:28]=2)[C:14](=[O:26])[CH:15]=[CH:16][CH2:17][O:18][CH2:19][CH2:20][N:21]2[CH2:25][CH2:24][CH2:23][CH2:22]2)=[CH:6][CH:5]=1.[NH2:37][OH:38].CO.[ClH:41]>C1COCC1.O.[OH-].[Na+]>[ClH:41].[O:31]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:28]=[C:27]1[N:13]([C:14](=[O:26])[CH:15]=[CH:16][CH2:17][O:18][CH2:19][CH2:20][N:21]1[CH2:22][CH2:23][CH2:24][CH2:25]1)[CH2:12][CH2:11][O:10][C:7]1[CH:8]=[CH:9][C:4]([C:3]([NH:37][OH:38])=[O:36])=[CH:5][CH:6]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 787HydroxylamineHCID 887MethanolHCID 69209252HCID 69209252, compound

Product 1

HCID 86600986HCID 86600986, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a solution of 4-{2-[3-benzofuran-2-yl-4-(2-pyrrolidin-1-ylethoxy)but-2-enoyl-amino]ethoxy}benzoic acid methyl ester (90 mg, 0.182 mmol) in THF (1 ml), a solution of hydroxylamine in 50% water (1 ml) and 1N NaOH (0.050 ul) were added. Methanol was added dropwise until a homogeneous solution was obtained and the reaction mixture was stirred overnight at rt. After cooling the mixture at 0° C., 6 N HCl was added until pH 7 was reached. The crude solid was filtered and purified by HPLC to give the title compound (17 mg) as white solid. LC/MS, M+1: 494.3; M−1: 492.2.

Workup

  1. customwas obtained
  2. temperatureAfter cooling the mixture at 0° C.
  3. filtrationThe crude solid was filtered
  4. custompurified by HPLC

Sources & evidence

ORD record
ord-0e63ccddd6254c518c27e022ced76093
Source dataset
uspto-grants-2008_05
Patent number
US07368476B2

Reaction notes

Loading…