Diisopropylethylamine → 2-Benzothiazol-2-ylmethylpiperidin-1-yl-[5-(4-fluorophenyl)-2-methylthiazol-4-yl]-methanone

HRID 2378020Notes

Reaction equation

HRID 2378020 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[CH2:7][C:8]1[S:9][C:10]2[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=2[N:12]=1.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.[F:50][C:51]1[CH:56]=[CH:55][C:54]([C:57]2[S:61][C:60]([CH3:62])=[N:59][C:58]=2[C:63](O)=[O:64])=[CH:53][CH:52]=1>CN(C=O)C>[S:9]1[C:10]2[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=2[N:12]=[C:8]1[CH2:7][CH:2]1[CH2:3][CH2:4][CH2:5][CH2:6][N:1]1[C:63]([C:58]1[N:59]=[C:60]([CH3:62])[S:61][C:57]=1[C:54]1[CH:55]=[CH:56][C:51]([F:50])=[CH:52][CH:53]=1)=[O:64]

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 223241255-(4-Fluorophenyl)-2-methyl-1,3-thiazole-4-carboxylic acidHCID 23146350HCID 23146350, compound

Product 1

HCID 231463432-Benzothiazol-2-ylmethylpiperidin-1-yl-[5-(4-fluorophenyl)-2-methylthiazol-4-yl]-methanone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Piperidin-2-ylmethylbenzothiazole, D30 (0.135 g), HATU (0.228 g), diisopropylethylamine (0.300 ml) and 5-(4-fluorophenyl)-2-methylthiazol-4-carboxylic acid (0.144 g) were dissolved in dry DMF and shaken at room temperature for 16 hours. The solvent was then evaporated and the residue partitioned between dichloromethane and brine. The organic layer was dried (MgSO4), evaporated and the residue chromatographed over silica gel. Elution with diethyl ether provided the title compound as a foam (220 mg).

Workup

  1. customThe solvent was then evaporated
  2. customthe residue partitioned between dichloromethane and brine
  3. dry with materialThe organic layer was dried (MgSO4)
  4. customevaporated
  5. customthe residue chromatographed over silica gel
  6. washElution with diethyl ether

Sources & evidence

ORD record
ord-0bcdf084f10146a59fd41af41386a6a1
Source dataset
uspto-grants-2008_12
Patent number
US07470710B2

Reaction notes

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