Diisopropylethylamine → Ethyl 2-amino-2-(2-(6-(benzo[d]thiazol-6-ylamino)-4-(isopropylamino)nicotinoyl)hydrazono)acetate

HRID 595389Notes

Reaction equation

HRID 595389 reaction equation
[S:1]1[C:5]2[CH:6]=[C:7]([NH:10][C:11]3[CH:19]=[C:18]([NH:20][CH:21]([CH3:23])[CH3:22])[C:14]([C:15]([OH:17])=O)=[CH:13][N:12]=3)[CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.[NH2:24][C:25](=[N:31][NH2:32])[C:26]([O:28][CH2:29][CH3:30])=[O:27].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[NH2:24][C:25](=[N:31][NH:32][C:15](=[O:17])[C:14]1[C:18]([NH:20][CH:21]([CH3:23])[CH3:22])=[CH:19][C:11]([NH:10][C:7]2[CH:8]=[CH:9][C:4]3[N:3]=[CH:2][S:1][C:5]=3[CH:6]=2)=[N:12][CH:13]=1)[C:26]([O:28][CH2:29][CH3:30])=[O:27]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 54084889ethyl (N'-aminocarbamimidoyl)formateHCID 896896766-(Benzo[d]thiazol-6-ylamino)-4-(isopropylamino)nicotinic acid

Product 1

HCID 123505650Ethyl 2-amino-2-(2-(6-(benzo[d]thiazol-6-ylamino)-4-(isopropylamino)nicotinoyl)hydrazono)acetate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 6-(benzo[d]thiazol-6-ylamino)-4-(isopropylamino)nicotinic acid (4) (500 mg, 3.8 mmol) and ethyl 2-amino-2-hydrazonoacetate (6) (3.8 mmol, 1 equiv.) in DMF (10 mL), HATU (7.63 mmol, 2 equiv.) and DIPEA (15.2 mmol, 4 equiv.) were added and stirred for 4 h. The reaction mixture was concentrated under reduced pressure to remove excess of DMF. The residue obtained was partitioned between water and EtOAc. The organic layer was separated, dried over Na2SO4, filtered and concentrated. The crude material obtained was purified by column chromatography through silica gel and MeOH: CHCl3 as eluent to afford the title compound.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customto remove excess of DMF
  3. customThe residue obtained
  4. customwas partitioned between water and EtOAc
  5. customThe organic layer was separated
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude material obtained
  10. customwas purified by column chromatography through silica gel and MeOH

Sources & evidence

ORD record
ord-d5bccad7c63d4e6ab4cba3745f8fbd8a
Source dataset
uspto-grants-2016_01
Patent number
US09242975B2

Reaction notes

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