Hydrochloric Acid → HCID 86755893, compound

HRID 365930Notes

Reaction equation

HRID 365930 reaction equation
C([N:8]1[CH2:11][CH2:10][C@H:9]1[CH2:12][O:13][C:14]1[CH:15]=[N:16][C:17]([Cl:26])=[C:18]([CH2:20][NH:21][C:22](=[O:25])[CH2:23][Cl:24])[CH:19]=1)(OC(C)(C)C)=O.Cl.Cl.CCOCC>CO>[ClH:24].[NH:8]1[CH2:11][CH2:10][C@H:9]1[CH2:12][O:13][C:14]1[CH:15]=[N:16][C:17]([Cl:26])=[C:18]([CH2:20][NH:21][C:22](=[O:25])[CH2:23][Cl:24])[CH:19]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10953452Ether hydrochlorideHCID 86755895HCID 86755895, compound

Product 1

HCID 86755893HCID 86755893, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The product of step 211a (0.34 g, 0.80 mmol) was deprotected and isolated as the free base in 37% yield according to the procedure of Example 20b, followed by conversion to the monohydrochloride with HCl/Et2O: [α]D23 +16.82 (c 0.3, MeOH); 1H NMR (D2O, 300 MHz) δ 2.72 (q, J=8.5, 16.5 Hz, 2H), 4.07-4.43 (m, 4H), 4.45 (s, 2H), 4.48 (d, J=4.5 Hz, 2H), 4.81 (m, 1H), 7.53 (d, J=3.0 Hz, 1H), 8.08 (d, J=3.0 Hz, 1H); MS (CI/NH3) m/z 304 (M+H)+. Anal. Calcd for C12H15Cl2N3O2.HCI: C, 42.31; H, 4.73; N, 12.33. Found: C, 42.34; H, 5.00; N, 12.25.

Workup

  1. customisolated as the free base in 37% yield

Sources & evidence

ORD record
ord-fa64eef2312c4789b52b98d3273160a2
Source dataset
uspto-grants-2000_10
Patent number
US06127386

Reaction notes

Loading…