N-methyl-2-pyrrolidone → HCID 59406376, compound

HRID 2060079Notes

Reaction equation

HRID 2060079 reaction equation
C(OC(=O)[NH:7][C:8]1[S:9][C:10]2[CH:16]=[C:15]([CH2:17][NH2:18])[CH:14]=[CH:13][C:11]=2[N:12]=1)(C)(C)C.[CH:20](N(CC)C(C)C)(C)C.CN([C:32]([O:36]N1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH3:53][N:54]1[C:58](=[O:59])[CH2:57][CH2:56][CH2:55]1>C(OCC)(=O)C>[NH2:7][C:8]1[S:9][C:10]2[CH:16]=[C:15]([CH2:17][NH:18][C:32]([C:53]3[CH:55]=[CH:56][CH:57]=[C:58]([O:59][CH3:20])[N:54]=3)=[O:36])[CH:14]=[CH:13][C:11]=2[N:12]=1

Participants

6

Reactant 4

HCID 13387N-methyl-2-pyrrolidoneHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 59588368HCID 59588368, compound

Product 1

HCID 59406376HCID 59406376, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 6-hydroxypicolinic 265 (0.14 g, 1.0 mmol, 1.00 equiv), (6-aminomethyl-benzothiazol-2-yl)-carbamic acid tert-butyl ester (0.28 g, 1.0 mmol, 1.0 equiv) and N,N-diisopropylethylamine (0.35 mL, 2.0 mmol, 2.0 equiv) in NMP (2.5 mL) at room temperature was added HATU (0.38 g, 1.0 mmol, 1.0 equiv) in one portion. The reaction mixture was stirred at room temperature for 2 hours, diluted with ethyl acetate and washed with water, brine, dried (sodium sulfate) and concentrated affording 6-methoxy-pyridine-2-carboxylic acid (2-amino-benzothiazol-6-ylmethyl)-amide 266. LCMS: (MH—C4H8)+=345.0 (1.55 min). (See Table 24).

Workup

  1. washwashed with water, brine
  2. dry with materialdried (sodium sulfate)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-065ae7a86ffd4fd4b0b8cedc5b4d21de
Source dataset
uspto-grants-2012_10
Patent number
US08278337B2

Reaction notes

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