Hydrochloric Acid → HCID 22000406, compound

HRID 917507Notes

Reaction equation

HRID 917507 reaction equation
[N:1]1[C:5]2[C:6]3[CH:14]=[CH:13][CH:12]=[CH:11][C:7]=3[O:8][CH2:9][CH2:10][C:4]=2[S:3][C:2]=1[NH:15][CH2:16][CH:17]1[CH2:22][CH2:21][CH:20]([NH:23][C:24](=O)[CH3:25])[CH2:19][CH2:18]1.Cl.[OH-].[Na+]>C1COCC1>[CH2:24]([NH:23][CH:20]1[CH2:21][CH2:22][CH:17]([CH2:16][NH:15][C:2]2[S:3][C:4]3[CH2:10][CH2:9][O:8][C:7]4[CH:11]=[CH:12][CH:13]=[CH:14][C:6]=4[C:5]=3[N:1]=2)[CH2:18][CH2:19]1)[CH3:25]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 22000430HCID 22000430, compound

Product 1

HCID 22000406HCID 22000406, compoundYield 69.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of N1-{4-[(4,5-dihydro-benzo[2,3]oxepino[4,5-d][1,3]thiazol-2-ylamino)-methyl]cyclohexyl}acetamide (0.380 g, 1.02 mmol) in anhydrous THF (4 ml) was added 1M BH3 in THF (5.0 ml, 5.0 mmol). The solution was stirred at room temperature overnight. 4N HCl (12 ml) was added slowly and stirring continued for 15 minutes. The resulting solution was made basic (pH˜9) with 2N NaOH. The cloudy solution was extracted with EtOAc and the organic layer washed with water. Removal of the solvent in vacuo, gave 69% (252 mg) of the product as a solid which was used without further purification: 1H-NMR (CDCl3) δ 0.96 (4H, m), 1.08 (3H, t, J=7.1 Hz), 1.47 (1H, m), 1.76 (2H, d, J=12.1 Hz), 1.90 (2H, m), 2.37 (2H, m), 2.63 (2H, q, J=7.0 Hz), 3.05 (2H, t, J=5.7 Hz), 3.11 (2H, t, J=5.1 Hz), 4.28 (2H, t, J=5.2 Hz), 5.73 (1H, broad t), 6.96 (1H, dd, J=0.9 Hz, 7.7 Hz), 7.10 (2H, m), 8.22 (1H, dd, J=1.3 Hz, 7.6 Hz); 358 (ESMS, MH+).

Workup

  1. stirringstirring
  2. waitcontinued for 15 minutes
  3. extractionThe cloudy solution was extracted with EtOAc
  4. washthe organic layer washed with water
  5. customRemoval of the solvent in vacuo

Sources & evidence

ORD record
ord-cfdc1d979cd24d8fb217207c656b8fad
Source dataset
uspto-grants-2007_09
Patent number
US07273880B2

Reaction notes

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