Hydrochloride methanol → HCID 86711999, compound

HRID 1051358Notes

Reaction equation

HRID 1051358 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C@H:10]([NH:13][S@](C(C)(C)C)=O)[CH2:11][CH3:12])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].[ClH:20].CO>CCOCC>[ClH:20].[F:1][C:2]1[CH:3]=[C:4]([C@H:10]([NH2:13])[CH2:11][CH3:12])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9]

Participants

4

Reactant 2

HCID 21893726Hydrochloride methanolHCID 86711998HCID 86711998, compound

Product 1

HCID 86711999HCID 86711999, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 68 (1.5 g, 5.2 mmol) in Et2O (20 mL) at 0° C. was added 3N HCl/MeOH (5.0 mL, 15 mmol). After being stirred for 1.5 h, the solid was filtered and dried in vacuo to afford 900 mg (80%) of 70a. 1H NMR (500 MHz, DMSO-d6) δ 8.56 (s, 3H), 7.44 (dd, J=12.5, 2.0 Hz, 1H), 7.29-7.20 (m, 2H), 4.08 (m, 1H), 3.84 (s, 3H), 1.97 (m, 1H), 1.78 (m, 1H), 0.73 (t, J=7.0 Hz, 3H). LCMS (ESI) m/z: 167.1 [M+H−17]+.

Workup

  1. filtrationthe solid was filtered
  2. customdried in vacuo

Sources & evidence

ORD record
ord-f9750abd3b9d4bb5b56cfe97ded42e1e
Source dataset
uspto-grants-2016_07
Patent number
US09388171B2

Reaction notes

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