Hydrochloric Acid → HCID 22961865, compound

HRID 2305214Notes

Reaction equation

HRID 2305214 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:33])=[C:18]([CH2:20][NH:21][C:22](=[O:32])[C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([N+:29]([O-:31])=[O:30])[CH:24]=2)[CH:19]=1)(OC(C)(C)C)=O.C1(N)C(F)=C(F)C(F)=C(N)C=1F.[ClH:46].Cl.Cl.Cl.O>>[ClH:33].[ClH:46].[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:33])=[C:18]([CH2:20][NH:21][C:22](=[O:32])[C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([N+:29]([O-:31])=[O:30])[CH:24]=2)[CH:19]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 21885828Hydrate;hydrochlorideHCID 22961825HCID 22961825, compound

Product 1

HCID 22961865HCID 22961865, compoundYield 37%

Procedure

The product of step 212a (0.18 g, 0.40 mmol) was deprotected and isolated as the free base in 37% yield according to the procedure of Example 20b, followed by conversion to the dihydrochloride with excess HCl/Et20. 1H NMR (D2O, 300 MHz) δ 2.62-2.71 (q, J=8.5, 17.0 Hz, 2H), 4.01-4.18 (m, 2H), 4.41 (d, J=4.0 Hz, 2H), 4.65 (s, 2H), 4.88 (m, 1H), 7.57 (d, J=3.0 Hz, 1H), 7.78 (t, J=3.0 Hz, 1H), 8.09 (d, J=3.0 Hz, 1H), 8.19 (d, J=9.0 Hz, 1H), 8.43 (d, J=8.5 Hz, 1H), 8.61 (t, J=2.0 Hz, 1H); MS (CI/NH3) m/z 377 (M+H)+. Anal. Calcd for C17H17ClN4O4.2 HCl.H2O: C, 43.65; H, 4.53; N, 11.98. Found: C, 43.97; H, 4.54; N, 11.53.

Workup

  1. customisolated as the free base in 37% yield

Sources & evidence

ORD record
ord-f63ed09c2f7143bf9b8a7e8dd937e63d
Source dataset
uspto-grants-2002_08
Patent number
US06437138B1

Reaction notes

Loading…