Sodium Carbonate → HCID 178432519, compound

HRID 1419704Notes

Reaction equation

HRID 1419704 reaction equation
C([O-])([O-])=O.[Na+].[Na+].CS(O)(=O)=O.[C:12]([C:14]1[CH:19]=[CH:18][C:17]([C:20]2[S:21][C:22]([C:26]([NH:28][C@H:29]([CH3:46])[C@:30]([C:38]3[CH:43]=[CH:42][C:41]([F:44])=[CH:40][C:39]=3[F:45])([OH:37])[CH2:31][N:32]3[CH:36]=[N:35][CH:34]=[N:33]3)=[O:27])=[C:23]([CH3:25])[N:24]=2)=[CH:16][CH:15]=1)#[N:13].Cl.[NH2:48][OH:49]>O.C1COCC1>[F:45][C:39]1[CH:40]=[C:41]([F:44])[CH:42]=[CH:43][C:38]=1[C@@:30]([OH:37])([CH2:31][N:32]1[CH:36]=[N:35][CH:34]=[N:33]1)[C@H:29]([NH:28][C:26]([C:22]1[S:21][C:20]([C:17]2[CH:18]=[CH:19][C:14]([C:12]([NH:48][OH:49])=[NH:13])=[CH:15][CH:16]=2)=[N:24][C:23]=1[CH3:25])=[O:27])[CH3:46]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 10031340HCID 10031340, compound

Product 1

HCID 178432519HCID 178432519, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of Na2CO3 (0.72 g, 6.77 mmol) in a mixture of H2O (5 mL) and THF (5 mL) was added (1R,2R)-2-(4-cyanophenyl)-N-[2-(2,4-difluorophenyl)-2-hydroxy-1-methyl-3-(1H-1,2,4-triazol-1 -yl)propyl]-4-methyl-thiazole-5-carboxamide methanesulfonate (0.5 g, 0.84 mmol, obtained in example 31) and hydroxylamine hydrochloride (0.29 g, 4.23 mmol). The reaction mixture was stirred at room temperature overnight, and was then concentrated and the aqueous residue extracted with CHCl3. The organic phase was separated, dried over Na2SO4, filtered and the filtrate was concentrated to a solid. Purification by flash chromatography afforded the title compound as a pale yellow solid: mp 135°-148° C.; 1H NMR (300 MHz, MeOH--d4) δ (MeOH--d4) 8.24 (s, 1H, triazole), 8.03 (dt, Jt =1.6, Jd =8.5, 2H, arom), 7.78 (dt, Jt =1.6, Jd =8.5, 2H, arom), 7.71 (s, 1H, triazole), 7.38 (dt, Jd =6.5, Jt =8.8, 1H, arom), 6.97 (ddd, J=2.4, J=8.7, J=11.5, 1H, arom), 6.84 (dt, Jd =2.1, Jt =8.0, 1H, arom), 5.00 (q, J=7, 1H, CHMe), 4.99 (d, J=14.3, 1H, TrCH(H)), 4.58 (d, J=14.3, 1H, TrCH(H)), 2.74 (s, 3H, thiazole-Me), 1.05 (d, J=7, 3H, MeCH); MS 496 (M+ -NH2); [α]D =-77.2° (c 1, MeOH). Analysis calculated for C24H23F2N7O3S.H2O: C 52.84; H 4.62; N 17.97; S 5.88 Found: C 53.48; H 4.61; N 17.19; S 5.34.

Workup

  1. concentrationwas then concentrated
  2. extractionthe aqueous residue extracted with CHCl3
  3. customThe organic phase was separated
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated to a solid
  7. customPurification by flash chromatography

Sources & evidence

ORD record
ord-5dc8aa567795496dbff6edb2182b1298
Source dataset
uspto-grants-1999_03
Patent number
US05888941

Reaction notes

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