Water → HCID 59190763, compound

HRID 418347Notes

Reaction equation

HRID 418347 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:34]=[CH:35][C:36]=1[O:37][CH3:38])[C:5]([NH:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15](=[O:33])[NH:16][C:17]2[S:18][C:19]3[CH2:25][C@H:24]([NH:26]C(=O)C(F)(F)F)[CH2:23][CH2:22][C:20]=3[N:21]=2)[CH:10]=1)=[O:6].O.C([O-])([O-])=O.[K+].[K+]>CO.CN(C=O)C>[NH2:26][C@@H:24]1[CH2:23][CH2:22][C:20]2[N:21]=[C:17]([NH:16][C:15]([C:11]3[CH:10]=[C:9]([CH:14]=[CH:13][CH:12]=3)[CH2:8][NH:7][C:5](=[O:6])[C:4]3[CH:34]=[CH:35][C:36]([O:37][CH3:38])=[C:2]([Cl:1])[CH:3]=3)=[O:33])[S:18][C:19]=2[CH2:25]1

Participants

6

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 59190740HCID 59190740, compound

Product 1

HCID 59190763HCID 59190763, compoundYield 77.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
55 °C

Procedure

Dissolved 3-chloro-4-methoxy-N-{3-[(R)-6-(2,2,2-trifluoro-acetylamino)-4,5,6,7-tetrahydro-benzothiazol-2-ylcarbamoyl]-benzyl}-benzamide (520 mg, 0.92 mmol) in 5 mL of MeOH and added 5 mL of H2O. To this was added K2CO3 (500 mg, 3.62 mmol) and the mixture was heated overnight at 55° C. LC-MS analysis indicated the desired material. Dissolved in 5 mL of DMF and purified via prep HPLC (5%-70% CH3CN/H2O) to give 334.6 mg of N-[3-((R)-6-Amino-4,5,6,7-tetrahydro-benzothiazol-2-ylcarbamoyl)-benzyl]-3-chloro-4-methoxy-benzamide. MS, electrospray 471.2 (M+H).

Workup

  1. custompurified via prep HPLC (5%-70% CH3CN/H2O)

Sources & evidence

ORD record
ord-3f11bb6f9a7a4acdad2d85f0c085e225
Source dataset
uspto-grants-2012_01
Patent number
US08093266B2

Reaction notes

Loading…