Water → HCID 178483361, compound

HRID 1007554Notes

Reaction equation

HRID 1007554 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][NH:11][C@H:12]2[CH2:17][CH2:16][C@H:15]([C:18]3[CH:27]=[CH:26][C:21]4[NH:22][C:23](=[O:25])[S:24][C:20]=4[CH:19]=3)[CH2:14][CH2:13]2)=[CH:4][CH:3]=1.O.[C:29](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>CO>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][N:11]([CH3:29])[C@H:12]2[CH2:17][CH2:16][C@H:15]([C:18]3[CH:27]=[CH:26][C:21]4[NH:22][C:23](=[O:25])[S:24][C:20]=4[CH:19]=3)[CH2:14][CH2:13]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 5049666Sodium triacetoxyborohydrideHCID 178518613HCID 178518613, compound

Product 1

HCID 178483361HCID 178483361, compoundYield 20.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 6-{trans-4-[3-(4-fluorophenyl)-propylamino]cyclohexyl}-3H-benzthiazol-2-one (0.24 g, 0.67 mmol) in MeOH (10 mL) containing H2O (0.5 mL) was added p-formaldehyde (0.1 g, 3.3 mmol). The reaction mixture was stirred for 3 hours. Sodium triacetoxyborohydride (0.2 g, 0.9 mmol) was added, and the mixture was stirred overnight. Solid NaOH was added until the solution became clear. The reaction mixture was concentrated under reduced pressure to give a yellow oil. Purification by flash chromatography (eluent 9.5:1:1 CH2Cl2:MeOH:NH4OH) gave 6-(trans-4-{[3-(4-fluorophenyl)-propyl]methylamino}cyclohexyl)-3H-benzthiazol-2-one (55 mg, 15%), as a pale yellow solid: mp 256-261° C.; IR (KBr): 2942, 1683, 1509 cm−1; 1H NMR (500 MHz, DMSO-d6): δ 7.41 (s, 1H), 7.31-7.03 (m, 6H), 3.29 (m, 2H), 3.01 (m, 2H), 2.70 (s, 3H), 2.64 (m, 2H), 2.11 (m, 1H), 2.08 (m, 1H), 1.99 (m, 2H), 1.87 (m, 2H), 1.98-1.61 (m, 4H); API-MS (m/z): 399 [M+H]+; calcd for C23H27FN2OS, 399.1906; found, 399.1909; HPLC: method A, 5.85 minutes (>99%); method B, 11.48 minutes (>99%); Anal. Calcd for C23H27FN2OS.HCl.0.75NaCl: C, 57.69; H, 5.89; N, 5.85. Found: C, 57.72; H, 5.96;N, 5.51.

Workup

  1. stirringthe mixture was stirred overnight
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customto give a yellow oil
  4. customPurification by flash chromatography (eluent 9.5:1:1 CH2Cl2:MeOH:NH4OH)

Sources & evidence

ORD record
ord-93730d3ddf6648c1b5e49b2f313cb660
Source dataset
uspto-grants-2004_09
Patent number
US06794402B2

Reaction notes

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