N,N-Dimethyl-1,3-propanediamine → 2-(3,3-Dimethylbutyrylamino)-4,5,6,7-tetrahydrobenzthiazol-4-carboxylic acid(3-dimethylaminopropyl)amide

HRID 1394106Notes

Reaction equation

[CH3:1][C:2]([CH3:20])([CH3:19])[CH2:3][C:4]([NH:6][C:7]1[S:8][C:9]2[CH2:15][CH2:14][CH2:13][CH:12]([C:16]([OH:18])=O)[C:10]=2[N:11]=1)=[O:5].[CH3:21][N:22]([CH3:27])[CH2:23][CH2:24][CH2:25][NH2:26]>C(Cl)Cl.O>[CH3:21][N:22]([CH3:27])[CH2:23][CH2:24][CH2:25][NH:26][C:16]([CH:12]1[C:10]2[N:11]=[C:7]([NH:6][C:4](=[O:5])[CH2:3][C:2]([CH3:1])([CH3:20])[CH3:19])[S:8][C:9]=2[CH2:15][CH2:14][CH2:13]1)=[O:18]

Participants

Conditions

Temperature: 0 °C

Procedure

1,1-Carbonyldiimidazole (CDI, 87 mg, 0.537 mmol) was added to a solution of 2-(3,3-dimethylbutyrylamino)-4,5,6,7-tetrahydrobenzthiazol-4-carboxylic acid (144 mg, 0.486 mmol) in CH2Cl2 (10 mL), and the resultant mixture was stirred for a period of 2 hours at room temperature. Following cooling of the suspension to 0° C., N,N-dimethyl-1,3-propanediamine (51 mg, 0.50 mmol), dissolved in CH2Cl2 (10 mL), was added dropwise over a period of 10 minutes. Following stirring for 1 hour at 0° C. and overnight at room temperature, a few drops of water were added, and the resultant mixture was extracted with CH2Cl2 (3×10 mL). Following drying of the organic phase over Na2SO4 and filtration, the solvent was removed and the residue was purified via column chromatography. The product 2-(3,3-dimethylbutyrylamino)-4,5,6,7-tetrahydrobenzthiazol-4-carboxylic acid(3-dimethylaminopropyl)amide was obtained in a yield of 125 mg (corresponding to 68% of theory).

Workup

additionwas added dropwise over a period of 10 minutes
extractionthe resultant mixture was extracted with CH2Cl2 (3×10 mL)
dry with materialFollowing drying of the organic phase over Na2SO4 and filtration
customthe solvent was removed
customthe residue was purified via column chromatography

Sources & evidence

ORD record: ord-72171aad49cc44ac959597bba1197069
Source dataset: uspto-grants-2008_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07348347B2

Reaction notes

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