Diisopropylethylamine → HCID 86622761, compound

HRID 1020262Notes

Reaction equation

HRID 1020262 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:9]([C:10]([OH:12])=O)=[C:8]([CH3:13])[O:7][N:6]=1)=[O:4].C(N(C(C)C)CC)(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[F:45][C:46]1[CH:47]=[C:48]([CH:62]=[CH:63][CH:64]=1)[CH2:49][NH:50][C:51]([NH:53][C:54]1[S:55][CH:56]=[C:57]([CH2:59][NH:60][CH3:61])[N:58]=1)=[O:52]>CN(C)C=O.O>[F:45][C:46]1[CH:47]=[C:48]([CH:62]=[CH:63][CH:64]=1)[CH2:49][NH:50][C:51](=[O:52])[NH:53][C:54]1[S:55][CH:56]=[C:57]([CH2:59][N:60]([CH3:61])[C:10]([C:9]2[C:5]([C:3]([O:2][CH3:1])=[O:4])=[N:6][O:7][C:8]=2[CH3:13])=[O:12])[N:58]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 58055087HCID 58055087, compoundHCID 69185303HCID 69185303, compound

Product 1

HCID 86622761HCID 86622761, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

3-(methoxycarbonyl)-5-methylisoxazole-4-carboxylic acid (1 mmol) was dissolved in N,N-dimethylformamide (5 ml), then diisopropylethylamine (1.2 eq.) and TBTU (1.2 eq) was added and stirred at room temperature for 5 minutes. 1-(3-fluorobenzyl)-3-(4-((methylamino)methyl)thiazol-2-yl)urea (1.0 mmol) was added and stirred overnight. Water (20 ml) was added to the reaction. The precipitate was filtered, washed with water and dried. The crude was purified by column using 0-100% gradient of 10% MeOH/EtOAc and hexanes to afford methyl 4-(((2-(3-(3-fluorobenzyl)ureido)thiazol-4-yl)methyl)(methyl)carbamoyl)-5-methylisoxazole-3-carboxylate.

Workup

  1. stirringstirred overnight
  2. filtrationThe precipitate was filtered
  3. washwashed with water
  4. customdried
  5. customThe crude was purified by column

Sources & evidence

ORD record
ord-b18415a7e52a45ae8b8752b91680ae27
Source dataset
uspto-grants-2014_05
Patent number
US08716320B2

Reaction notes

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