Dimethylformamide → methyl 2-({2-[(tert-butoxycarbonyl)amino]-4-methoxyphenyl}carbamoyl)-N-phenyl-6,7-dihydro[1,3]thiazolo[5,4-c]pyridine-5(4H)-carbimidothioate

HRID 2093068Notes

Reaction equation

HRID 2093068 reaction equation
[CH3:1][S:2]/[C:3](=[N:16]\[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)/[N:4]1[CH2:9][CH2:8][C:7]2[N:10]=[C:11]([C:13]([OH:15])=O)[S:12][C:6]=2[CH2:5]1.[C:23]([O:27][C:28](=[O:39])[NH:29][C:30]1[CH:35]=[CH:34][C:33](OC)=[CH:32][C:31]=1[NH2:38])([CH3:26])([CH3:25])[CH3:24].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.CN([CH:64]=[O:65])C>C(N(CC)CC)C>[C:23]([O:27][C:28]([NH:29][C:30]1[CH:35]=[C:34]([O:65][CH3:64])[CH:33]=[CH:32][C:31]=1[NH:38][C:13]([C:11]1[S:12][C:6]2[CH2:5][N:4]([C:3]([S:2][CH3:1])=[N:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:9][CH2:8][C:7]=2[N:10]=1)=[O:15])=[O:39])([CH3:24])([CH3:25])[CH3:26]

Participants

7

Reactant 5

HCID 6228DimethylformamideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 10752410tert-butyl N-(2-amino-4-methoxyphenyl)carbamateHCID 178503854HCID 178503854, compound

Product 1

HCID 66864416methyl 2-({2-[(tert-butoxycarbonyl)amino]-4-methoxyphenyl}carbamoyl)-N-phenyl-6,7-dihydro[1,3]thiazolo[5,4-c]pyridine-5(4H)-carbimidothioate

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A suspension of 5-[(Z)-(methylthio)(phenylimino)methyl]-4,5,6,7-tetrahydro[1,3]thiazolo[5,4-c]pyridine-2-carboxylic acid obtained from step III of example 116 (1 eq), (2-amino-4-methoxy-phenyl)-carbamic acid tert-butyl ester (1.2 eq), EDCI (1.2 eq), HOBt (1.2 eq) and triethylamine in DMF were stirred at room temperature for 15 h. Solvent was evaporated and the residue was purified by either column chromatography or preparative HPLC to afford methyl 2-({2-[(tert-butoxycarbonyl)amino]-4-methoxyphenyl}carbamoyl)-N-phenyl-6,7-dihydro[1,3]thiazolo[5,4-c]pyridine-5(4H)-carbimidothioate.

Workup

  1. customSolvent was evaporated
  2. customthe residue was purified by either column chromatography or preparative HPLC

Sources & evidence

ORD record
ord-bb9aed13fd134e5cad1b9424dfda8e4a
Source dataset
uspto-grants-2013_05
Patent number
US08440830B2

Reaction notes

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