4-Methylmorpholine → HCID 59369645, compound

HRID 45392Notes

Reaction equation

HRID 45392 reaction equation
[CH2:1]([NH:8][C:9]([C:11]1[S:15][C:14]([NH2:16])=[N:13][C:12]=1[CH3:17])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN1CCOCC1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.[N:52]1([CH2:57][C:58]2[CH:66]=[CH:65][C:61]([C:62](O)=[O:63])=[CH:60][CH:59]=2)[CH:56]=[CH:55][CH:54]=[N:53]1>CN(C)C=O>[N:52]1([CH2:57][C:58]2[CH:66]=[CH:65][C:61]([C:62]([NH:16][C:14]3[S:15][C:11]([C:9]([NH:8][CH2:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)=[O:10])=[C:12]([CH3:17])[N:13]=3)=[O:63])=[CH:60][CH:59]=2)[CH:56]=[CH:55][CH:54]=[N:53]1

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 210824N-Benzyl-2-imino-4-methyl-2,3-dihydro-1,3-thiazole-5-carboximidic acidHCID 64842684-(1H-pyrazol-1-ylmethyl)benzoic acid

Product 1

HCID 59369645HCID 59369645, compoundYield 136.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-amino-4-methylthiazole-5-carboxylic acid benzylamide (0.47 g, 1.88 mmol), and N-methylmorpholine (0.23 mL, 2.08 mmol) in N,N-dimethylformamide (20 mL) at 0° C. was added (benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate (0.42 g, 2.09 mmol) and 4-pyrazol-1-ylmethyl-benzoic acid (0.42 g, 2.09 mmol). The resultant solution was allowed to warm to ambient temperature over 18 h, and concentrated in vacuo. The crude product was purified by flash column chromatography eluting with methanol/dichloromethane (0/100 to 30/70) to afford the title compound (1.11 g); MS (ES+) m/z 432 (M+1).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe crude product was purified by flash column chromatography
  3. washeluting with methanol/dichloromethane (0/100 to 30/70)

Sources & evidence

ORD record
ord-679638fe8dc74960a489277dade3093b
Source dataset
uspto-grants-2013_09
Patent number
US08541457B2

Reaction notes

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