HCID 11233520, compound → HCID 86035666, compound

HRID 495131Notes

Reaction equation

HRID 495131 reaction equation
C(OC(=O)[NH:7][CH2:8][CH2:9][CH2:10][O:11][C:12]1[C:17]2[C:18]([Cl:22])=[CH:19][CH:20]=[CH:21][C:16]=2[O:15][C:14](=[O:23])[CH:13]=1)(C)(C)C.Cl.O1CCOCC1>>[ClH:22].[NH2:7][CH2:8][CH2:9][CH2:10][O:11][C:12]1[C:17]2[C:18]([Cl:22])=[CH:19][CH:20]=[CH:21][C:16]=2[O:15][C:14](=[O:23])[CH:13]=1

Participants

3

Reactant 2

HCID 11233520HCID 11233520, compoundHCID 204431481,4-Dioxane hydrochloride

Product 1

HCID 86035666HCID 86035666, compoundYield 71.4%

Procedure

[3-(5-Chloro-2-oxo-2H-1-benzopyran-4-yloxy)-propyl]-carbamic acid tert-butyl ester (24a) (0.079 g, 0.22 mmol) is treated with 4N HCl/dioxane for several minutes during which time a precipitate is formed. The solventVHCl is removed under reduced pressure. The residue is recrystallized from MeOH/EtOAc followed by a second recrystallization from EtOH to afford the title compound as the hydrochloric acid salt (22.8 mg, 41%). 1H NMR (DMSO-d6, 300 MHz) δ 7.94 (3H, brs), 7.62 (1H, t, J=8.25 Hz), 7.43 (2H, m), 5.94 (1H, s), 4.29 (2H, t, J=5.75 Hz), 3.04 (2H, t, J=7 Hz), 2.14 (2H, m); MS (ESI, Pos.) calcd for C12H12ClNO3 m/z [M+H]=254.0, found 254.1.

Workup

  1. customis formed
  2. customThe solventVHCl is removed under reduced pressure
  3. customThe residue is recrystallized from MeOH/EtOAc
  4. customfollowed by a second recrystallization from EtOH

Sources & evidence

ORD record
ord-12efb1970e5143508271d7597c778222
Source dataset
uspto-grants-2009_05
Patent number
US07538233B2

Reaction notes

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