Diisopropylcarbodiimide → HCID 67957833, compound

HRID 450344Notes

Reaction equation

HRID 450344 reaction equation
[CH2:1]([O:3][C:4](=[O:24])[C:5]1[CH:10]=[C:9]([NH2:11])[C:8]([NH:12][CH3:13])=[N:7][C:6]=1[N:14]1[CH2:19][CH2:18][CH:17]([C:20]([F:23])([F:22])[F:21])[CH2:16][CH2:15]1)[CH3:2].[Cl:25][C:26]1[C:39]([N:40]=[C:41]=S)=[C:38]([Cl:43])[CH:37]=[CH:36][C:27]=1[CH2:28][NH:29][C:30](=[O:35])[C:31]([CH3:34])([CH3:33])[CH3:32].CC(C)N=C=NC(C)C>CC#N>[CH2:1]([O:3][C:4]([C:5]1[CH:10]=[C:9]2[N:11]=[C:41]([NH:40][C:39]3[C:38]([Cl:43])=[CH:37][CH:36]=[C:27]([CH2:28][NH:29][C:30](=[O:35])[C:31]([CH3:34])([CH3:33])[CH3:32])[C:26]=3[Cl:25])[N:12]([CH3:13])[C:8]2=[N:7][C:6]=1[N:14]1[CH2:19][CH2:18][CH:17]([C:20]([F:23])([F:21])[F:22])[CH2:16][CH2:15]1)=[O:24])[CH3:2]

Participants

5

Reactant 3

HCID 12734DiisopropylcarbodiimideHCID 56840192N-[(2,4-dichloro-3-isothiocyanatophenyl)methyl]-2,2-dimethylpropanamideHCID 67957760HCID 67957760, compound

Product 1

HCID 67957833HCID 67957833, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A mixture of 6-methylamino-5-amino-2-(4-trifluoromethyl-piperidinyl)-nicotinic acid ethylester (2.80 g, 7.92 mmol), N-(2,4-dichloro-3-isothiocyanato-benzyl)-2,2-dimethyl-propionamide (2.76 g, 8.72 mmol) and MeCN (60 mL) is stirred overnight, concentrated and triturated with MeCN and Et2O. The resulting solid is diluted with 60 mL MeCN and DIC (1.06 mL, 6.8 mmol) is added and it is stirred for 3 h at 60° C. The crude mixture is concentrated, diluted with EtOAc, washed with water, dried with Na2SO4, filtered, concentrated and purified by flash chromatography (silica; PE:EtOAc 3:1->1:1). Yield: 4.04 g. HPLC Rt=1.56 min (method D). MS m/z: 629 [M+H]+.

Workup

  1. concentrationconcentrated
  2. customtriturated with MeCN and Et2O
  3. additionis added
  4. stirringit is stirred for 3 h at 60° C
  5. concentrationThe crude mixture is concentrated
  6. additiondiluted with EtOAc
  7. washwashed with water
  8. dry with materialdried with Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated
  11. custompurified by flash chromatography (silica; PE:EtOAc 3:1->1:1)

Sources & evidence

ORD record
ord-78b8e7591a4c4f059cbe2d59814039ae
Source dataset
uspto-grants-2013_07
Patent number
US08486968B2

Reaction notes

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