Hydrochloric Acid → HCID 69004873, compound

HRID 1909773Notes

Reaction equation

HRID 1909773 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:17][N:16]=1)=O)(C)(C)C.[ClH:28]>C(OCC)C>[ClH:28].[CH2:21]([C:18]1[CH:19]=[CH:20][C:15]([O:14][CH2:13][C@@H:9]2[CH2:10][CH2:11][CH2:12][NH:8]2)=[N:16][CH:17]=1)[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 69001877HCID 69001877, compound

Product 1

HCID 69004873HCID 69004873, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To the product from step 3 (25 mg, 0.068 mmol) was added 2N HCl (3 mL) in diethyl ether. The resulting mixture was stirred at rt for 2 h. The solvent was removed to give the title compound (20 mg, 97%). MS; m/z 269 (M+H)>90% 1H NMR (DMSO-d6, 400 MHz) δ 1.59-2.12 (4H, m), 3.19 (2H, m), 3.88 (2H, s), 4.34 (1H, d, J=8.0 Hz), 4.48 (1H, dd, J1=4.0 Hz, J2=11.6 Hz), 6.80 (1H, d, J=8.4 Hz), 7.17-7.30 (5H, m), 7.58 (1H, dd, J1=2.4 Hz, J2=8.4 Hz), 8.09 (1H, d, J=2.4 Hz), 8.93 (1NH, s), 9.49 (1NH, s).

Workup

  1. customThe solvent was removed

Sources & evidence

ORD record
ord-8136c5db142041078589439c2e6297df
Source dataset
uspto-grants-2013_12
Patent number
US08598359B2

Reaction notes

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