Hydrochloric Acid → HCID 22000429, compound

HRID 1976136Notes

Reaction equation

HRID 1976136 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)[CH2:25][O:26][CH3:27])[CH2:19][CH2:18]1.Cl.[OH-].[Na+]>C1COCC1>[CH3:27][O:26][CH2:25][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

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 22000431HCID 22000431, compound

Product 1

HCID 22000429HCID 22000429, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of N1-{4-[(4,5-dihydrobenzo[2,3]oxepino[4,5-d][1,3]thiazol-2- ylamino)-methyl]cyclohexyl}-2-methoxyacetamide (free-base) (0.450 g, 1.12 mmol) in anhydrous THF (5 ml) was added 5.0 ml 1M BH3 in THF (5.0 mmol). The solution was stirred at room temperature for 26 hours. 4N HCl (12 ml) was slowly added to the stirred solution and stirred continued for 1 hour. The solution was made basic with 2N NaOH (pH˜9) and was extracted with EtOAc. Upon evaporation of the solvent, 90% (390 mg) of the desired amine was obtained as a highly viscous colorless oil. The compound was converted to its dihydrochloride salt in chloroform with 1N HCl in Et2O. Evaporation of the solvent gave 460 mg of the salt as a slightly hygroscopic white solid: m.p. 243-245° C. (dec); 1H-NMR (CDCl3) δ 1.08 (4H, t, J=10.8 Hz), 1.6 (2H, broad), 1.91 (4H, m), 2.41 (1H, broad), 2.80 (2H, t, J=4.9 Hz), 3.15 (4H, m), 3.35 (3H, s), 3.49 (2H, t, J=5.3 Hz), 4.32 (2H, t, J=5.4 Hz), 5.13 (1H, broad t), 6.98 (1H, dd, J=1.3 Hz, 7.7 Hz), 7.12 (2H, m), 8.24 (1H, dd, J=1.6 Hz, 7.9 Hz); 388 (ESMS, MH+).

Workup

  1. stirringstirred
  2. waitcontinued for 1 hour
  3. extractionwas extracted with EtOAc
  4. customUpon evaporation of the solvent

Sources & evidence

ORD record
ord-d96a78329ac040309391f8357d8fb415
Source dataset
uspto-grants-2001_05
Patent number
US06225330B1

Reaction notes

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