Monomethyl terephthalate → methyl 4-((6-(2-(dimethylamino)-1-(1H-imidazol-1-yl)butyl)benzo[d]thiazol-2-yl)carbamoyl)benzoate

HRID 538877Notes

Reaction equation

HRID 538877 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=O)=[CH:7][CH:6]=1)=[O:4].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C.[CH3:47][N:48]([CH3:68])[CH:49]([CH2:66][CH3:67])[CH:50]([C:56]1[CH:65]=[CH:64][C:59]2[N:60]=[C:61]([NH2:63])[S:62][C:58]=2[CH:57]=1)[N:51]1[CH:55]=[CH:54][N:53]=[CH:52]1>CN(C=O)C>[CH3:47][N:48]([CH3:68])[CH:49]([CH2:66][CH3:67])[CH:50]([C:56]1[CH:65]=[CH:64][C:59]2[N:60]=[C:61]([NH:63][C:9]([C:8]3[CH:7]=[CH:6][C:5]([C:3]([O:2][CH3:1])=[O:4])=[CH:13][CH:12]=3)=[O:11])[S:62][C:58]=2[CH:57]=1)[N:51]1[CH:55]=[CH:54][N:53]=[CH:52]1

Participants

6

Reactant 4

HCID 15513Monomethyl terephthalateHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 547593306-(2-(dimethylamino)-1-(1H-imidazol-1-yl)butyl)benzo[d]thiazol-2-amine

Product 1

HCID 54760442methyl 4-((6-(2-(dimethylamino)-1-(1H-imidazol-1-yl)butyl)benzo[d]thiazol-2-yl)carbamoyl)benzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A mixture of 4-(methoxycarbonyl)benzoic acid (18 mg, 0.1 mmol), HATU (41.8 mg, 0.11 mmol), and diisopropylethylamine (39 mg) in DMF was stirred at RT for 5 min. A syn and anti mixture of 6-(2-(dimethylamino)-1-(1H-Imidazol-1-yl)butyl)benzo[d]thiazol-2-amine (31.5 mg, 0.1 mmol) in DMF was added and stirred at RT. DMF was evaporated and the residue was purified by PTLC using 10% methanol in DCM as eluent to afford the syn and anti isomers of methyl 4-((6-(2-(dimethylamino)-1-(1H-imidazol-1-yl)butyl)benzo[d]thiazol-2-yl)carbamoyl)benzoate. ESI: m/z 478.2 [M+1+].

Workup

  1. additionwas added
  2. stirringstirred at RT
  3. customDMF was evaporated
  4. customthe residue was purified by PTLC

Sources & evidence

ORD record
ord-47e63e71a127464fbc453336af68ab94
Source dataset
uspto-grants-2014_10
Patent number
US08865752B2

Reaction notes

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