Hydrochloric Acid → HCID 22000419, compound

HRID 1976143Notes

Reaction equation

HRID 1976143 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][CH3:26])[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)[CH2:25][CH3:26]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 22000389HCID 22000389, compound

Product 1

HCID 22000419HCID 22000419, compoundYield 77%

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}propanamide (0.405 g, 1.05 mmol) in anhydrous THF (4 ml) was added 1M BH3 in THF (5.5 ml, 5.5 mmol). The solution was stirred at room temperature for 52 hours. 4N HCl (12 ml) was added slowly and stirring continued for 30 minutes thereafter. The solution was poured into 2N NaOH (60 ml) and extracted with EtOAc. The extract was washed with 10% brine, separated and evaporated to yield 77% (300 mg) of the amine as a viscous golden oil: 1H-NMR (CDCl3) δ 0.88 (3H, t), 1.06 (2H, m), 1.38 (2H, m), 1.49 (2H, m), 1.80 (6H, m), 2.40 (1H, m), 2.58 (2H, t), 3.15 (2H, m), 3.63 (2H, t), 4.30 (2H, t), 5.12 (1H, m), 6.98 (1H, d), 7.11 (2H, m), 8.23 (1H, dd); 400 (ESMS, MH+).

Workup

  1. stirringstirring
  2. waitcontinued for 30 minutes
  3. extractionextracted with EtOAc
  4. washThe extract was washed with 10% brine
  5. customseparated
  6. customevaporated

Sources & evidence

ORD record
ord-d9d8cf4db71e42ac9a802959d999244b
Source dataset
uspto-grants-2001_05
Patent number
US06225330B1

Reaction notes

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