Methanol → HCID 22961855, compound

HRID 365879Notes

Reaction equation

HRID 365879 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][CH:17]=[C:18]([CH2:20][NH:21][C:22]([O:24][CH3:25])=[O:23])[CH:19]=1)(OC(C)(C)C)=O.C1(N)C(F)=C(F)C(F)=C(N)C=1F.[ClH:38].Cl.Cl.CCOCC.CO>CCOCC>[ClH:38].[ClH:38].[NH:8]1[CH2:11][CH2:10][C@H:9]1[CH2:12][O:13][C:14]1[CH:15]=[N:16][CH:17]=[C:18]([CH2:20][NH:21][C:22]([O:24][CH3:25])=[O:23])[CH:19]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 10953452Ether hydrochlorideHCID 22961820HCID 22961820, compound

Product 1

HCID 22961855HCID 22961855, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

The product of step 159a (0.23 g, 0.70 mmol) was deprotected and isolated as the free base in 99% yield according to the procedure of Example 20b, followed by conversion to the dihydrochloride with excess HCl/Et2O. [α]D23 +12.46 (c 0.1, MeOH); 1H NMR (D2O, 300 MHz) δ2.65-2.75 (m, 2H), 3.66 (s, 3H), 4.08-4.19 (m, 2H), 4.43 (s, 2H), 4.53-4.69 (m, 2H), 4.90 (m, 1H), 8.22 (s, 1H), 8.44 (s, 1H), 8.63 (d, J=3.0 Hz, 1H); MS (CI/NH3) m/z 252 (M+H)+. Anal. Calcd for C12H17N3O·2.5 HCl·1.5 H2O·0.4 Et2O: C, 40.93; H, 6.69; N, 10.53. Found: C, 40.96; H, 6.63; N, 10.46.

Workup

  1. customisolated as the free base in 99% yield

Sources & evidence

ORD record
ord-5ffb49c717364da9a2339963dff0675f
Source dataset
uspto-grants-2000_10
Patent number
US06127386

Reaction notes

Loading…