1,2-Dichloroethane → 3,4-Dimethoxy-N-[3-(5-methyl-4,5,6,7-tetrahydro-thiazolo[5,4-c]pyridin-2-ylcarbamoyl)-benzyl]-benzamide

HRID 418335Notes

Reaction equation

HRID 418335 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:19]=[CH:20][C:21]=1[O:22][CH3:23])[C:6]([NH:8][CH2:9][C:10]1[CH:11]=[C:12]([CH:16]=[CH:17][CH:18]=1)[C:13]([OH:15])=O)=[O:7].C(Cl)CCl.OC1C2N=NNC=2C=CC=1.CCN(C(C)C)C(C)C.[CH3:47][N:48]1[CH2:53][CH2:52][C:51]2[N:54]=[C:55]([NH2:57])[S:56][C:50]=2[CH2:49]1>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:19]=[CH:20][C:21]=1[O:22][CH3:23])[C:6]([NH:8][CH2:9][C:10]1[CH:18]=[CH:17][CH:16]=[C:12]([C:13](=[O:15])[NH:57][C:55]2[S:56][C:50]3[CH2:49][N:48]([CH3:47])[CH2:53][CH2:52][C:51]=3[N:54]=2)[CH:11]=1)=[O:7]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 81531DiisopropylethylamineHCID 23979985-methyl-4H,5H,6H,7H-[1,3]thiazolo[5,4-c]pyridin-2-amineHCID 448195433-[(3,4-Dimethoxy-benzoylamino)-methyl]-benzoic acidHCID 178418300HCID 178418300, compound

Product 1

HCID 250563723,4-Dimethoxy-N-[3-(5-methyl-4,5,6,7-tetrahydro-thiazolo[5,4-c]pyridin-2-ylcarbamoyl)-benzyl]-benzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Dissolved 3-[(3,4-dimethoxy-benzoylamino)-methyl]-benzoic acid (100 mg, 0.317 mmol), EDC (105 mg, 0.55 mmol) and hydroxybenzotriazole (84.2 mg, 0.55 mmol) in 1 mL of DMF. The mixture was stirred for 1 h. To this was added DIPEA (0.12 mL, 0.64 mmol) and 5-methyl-4,5,6,7-tetrahydro-thiazolo[5,4-c]pyridin-2-ylamine (107 mg, 0.63 mmol). The mixture was placed in a 60° C. bath with an Ar stream blowing over it. The mixture stirred 14 h resulting in a concentrated residue. LC-MS analysis indicated the desired product. Dissolved in 5 mL of DMF/H2O and purified via prep HPLC (5%-95% CH3CN/H2O) to give 121.9 mg of 3,4-dimethoxy-N-[3-(5-methyl-4,5,6,7-tetrahydro-thiazolo[5,4-c]pyridin-2-ylcarbamoyl)-benzyl]-benzamide. MS, electrospray 467.4 (M+H).

Workup

  1. customwas placed in a 60° C.
  2. stirringThe mixture stirred 14 h
  3. customresulting in a concentrated residue

Sources & evidence

ORD record
ord-32d14f6532a84498bc27c3786571f892
Source dataset
uspto-grants-2012_01
Patent number
US08093266B2

Reaction notes

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