Ammonium Chloride → HCID 21879376, compound

HRID 724696Notes

Reaction equation

HRID 724696 reaction equation
[C:1]([N:5]1[C:9](=[O:10])[CH:8]=[C:7]([C:11]2[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][NH:19][S:20]([C:23]3[CH:28]=[CH:27][C:26]([O:29][C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)=[CH:25][CH:24]=3)(=[O:22])=[O:21])=[CH:13][CH:12]=2)[S:6]1(=[O:37])=[O:36])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Li+].[Cl-].[NH4+]>O1CCCC1>[C:1]([N:5]1[C:9](=[O:10])[CH2:8][CH:7]([C:11]2[CH:12]=[CH:13][C:14]([CH2:17][CH2:18][NH:19][S:20]([C:23]3[CH:24]=[CH:25][C:26]([O:29][C:30]4[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=4)=[CH:27][CH:28]=3)(=[O:21])=[O:22])=[CH:15][CH:16]=2)[S:6]1(=[O:37])=[O:36])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 4148881Lithium borohydride2×HCID 21878718N-2-[4-(2-tert-butyl-1,1-dioxido-3-oxo-2,3-dihydroisothiazol-5-yl)phenyl]ethyl-4-phenoxybenzenesulfonamide

Product 1

HCID 21879376HCID 21879376, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

N-2-[4-(2-tert-Butyl-1,1-dioxido-3-oxo-2,3-dihydroisothiazol-5-yl)phenyl]ethyl-4-phenoxybenzenesulfonamide (26.0 mg, 0.0481 mmol) was dissolved in tetrahydrofuran (0.25 mL) and 2 M lithium tetrahydroborate in tetrahydrofuran (18 μL) was added to the reaction via syringe. After 10 minutes, 2 M lithium tetrahydroborate in tetrahydrofuran (18 μL) was added. After an additional 10 minutes, the reaction was added to 1 mL of saturated aqueous ammonium chloride and stirred vigorously. The reaction was chromatographed on a 21.2 mm Luna C 18 column using a 10–90% acetonitrile in water gradient with 0.05% trifluoroacetic acid at 12.5 mL per minute over a 15 minute period. The major fraction was evaporated to give a light orange solid (19 mg, 75%). 1H NMR (500 MHz, CDCl3): δ 7.77 (d, J=8.8 Hz, 2H), 7.42 (t, J=8.3 Hz, 2H), 7.34 (d, J=8.3 Hz, 2H), 7.23 (t, J=7.8 Hz, 1H), 7.13 (d, J=7.8 Hz, 2H), 7.07 (d, J=7.9 Hz, 2H), 7.03 (d, J=8.8 Hz, 2H), 4.65 (m, 1H), 4.29 (m, 1H), 3.95 (m, 1H), 3.75 (m, 1H) 3.40 (m, 1H), 2.60 (m, 1H), 2.24 (m, 1H), 1.31 (s, 9H); LCMS found for C27H34N3O6S2 (M+NH4)+: m/z 560.2.

Workup

  1. waitAfter an additional 10 minutes
  2. customThe reaction was chromatographed on a 21.2 mm Luna C 18 column
  3. customover a 15 minute
  4. customThe major fraction was evaporated

Sources & evidence

ORD record
ord-ec1f10f99add4485b6f7df432a268592
Source dataset
uspto-grants-2006_11
Patent number
US07141596B2

Reaction notes

Loading…