Hydrochloric Acid → HCID 22000385, compound

HRID 1976134Notes

Reaction equation

HRID 1976134 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][CH:16]1[CH2:21][CH2:20][CH:19]([CH2:22][NH:23][C:24](=O)[CH2:25][CH3:26])[CH2:18][CH2:17]1.CCOC(C)=O.Cl>C1COCC1>[CH2:24]([NH:23][CH2:22][CH:19]1[CH2:20][CH2:21][CH: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)[CH2:17][CH2:18]1)[CH2:25][CH3:26]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 22000421HCID 22000421, compound

Product 1

HCID 22000385HCID 22000385, compoundYield 72.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a solution of N1-{[4-(4,5-dihydrobenzo[2,3]oxepino[4,5-d][1,3]thiazol-2-ylamino)cyclohexyl]methyl}propanamide (0.380 g, 0.944 mmol) in anhydrous THF (7 ml) was added 1M BH3 in THF (2.0 ml, 2.0 mmol). The solution was stirred for several hours at room temperature. TLC (EtOAc) indicated reaction to be incomplete and an additional 2.5 ml 1M BH3 in THF was added to the solution which was then stirred overnight. 4N HCl (25 ml) was slowly added to the stirred solution and the solution was washed with EtOAc. The aqueous layer was made basic by addition of 20% NaOH. The resulting solution was extracted with EtOAc and the extract washed with water. Upon removal of the solvent, 72% (254 mg) of the product was obtained as a white solid: 1H-NMR (CDCl3) δ 0.88 (3H, t, J=7.3 Hz), 1.12 (4H, m), 1.43 (3H, m), 1.75 (2H, m), 2.14 (2H, m), 2.41 (2H, d, J=6.6 Hz), 2.51 (2H, t, J=7.4 Hz), 2.60 (1H, m), 3.10 (2H, t, J=5.0 Hz), 3.22 (1H, m), 4.27 (2H, t, J=5.0 Hz), 5.35 (1H, m), 6.95 (1H, d, J=7.6 Hz), 7.06 (2H, m), 8.20 (1H, d, J=7.3 Hz); 372 (ESMS, MH+).

Workup

  1. customreaction
  2. stirringwas then stirred overnight
  3. washthe solution was washed with EtOAc
  4. additionThe aqueous layer was made basic by addition of 20% NaOH
  5. extractionThe resulting solution was extracted with EtOAc
  6. washthe extract washed with water
  7. customUpon removal of the solvent

Sources & evidence

ORD record
ord-19329e060c074a68967ca1521ab999bf
Source dataset
uspto-grants-2001_05
Patent number
US06225330B1

Reaction notes

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