Hydrochloric Acid → HCID 86622759, compound

HRID 1020260Notes

Reaction equation

HRID 1020260 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[Cl:15][C:16]1[CH:17]=[C:18]([CH:32]=[CH:33][C:34]=1[Cl:35])[CH2:19][NH:20][C:21]([NH:23][C:24]1[S:25][CH:26]=[C:27]([CH2:29][NH:30][CH3:31])[N:28]=1)=[O:22].[CH3:36][C:37]1[C:41]([CH:42]=O)=[C:40]([CH3:44])[O:39][N:38]=1.Cl.C([O-])(O)=O.[Na+]>C(Cl)Cl.CO>[Cl:15][C:16]1[CH:17]=[C:18]([CH:32]=[CH:33][C:34]=1[Cl:35])[CH2:19][NH:20][C:21]([NH:23][C:24]1[S:25][CH:26]=[C:27]([CH2:29][N:30]([CH2:42][C:41]2[C:37]([CH3:36])=[N:38][O:39][C:40]=2[CH3:44])[CH3:31])[N:28]=1)=[O:22]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 2895763,5-Dimethyl-4-IsoxazolecarbaldehydeHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 25052051HCID 25052051, compound

Product 1

HCID 86622759HCID 86622759, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent3×

Procedure

Sodium triacetoxyborohydride (86 mg, 0.4 mmol, 2.0 eq) was added to a dichloromethane (2 mL) solution of 1-(3,4-Dichloro-benzyl)-3-(4-methylaminomethyl-thiazol-2-yl)-urea (Example 132, 70 mg, 0.2 mmol) and 3,5-dimethylisoxazole-4-carbaldehyde (33 mg, 0.25 mmol, 1.25 eq). After 16 hours of stirring, methanol (1 mL) and aqueous HCl (0.5 mL, 1N) were added. The mixture was neutralized with dilute NaHCO3 solution. An aqueous work-up with dichloromethane and a chromatography (silica 0-3% MeOH in CH2Cl2) afforded the title compound. 1H NMR (400 MHz, CDCl3): 7.36 (m, 2H), 7.10 (dd, 1H), 6.64 (s, 1H), 4.32 (d, 2H), 3.46 (s, 3H), 3.21 (s, 3H), 2.28 (s, 3H), 2.16 (s, 3H), 2.07 (s, 3H). MS (ES+): M/Z 454 (M+1).

Sources & evidence

ORD record
ord-2ea16e6ea1ef45d288cebec26d4e1c41
Source dataset
uspto-grants-2014_05
Patent number
US08716320B2

Reaction notes

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