Diisopropylethylamine → HCID 9911963, compound

HRID 2376696Notes

Reaction equation

HRID 2376696 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:12][C:11]([CH3:13])=[N:10][C:9]=2[C:14]([OH:16])=O)=[CH:4][CH:3]=1.C(N(CC)C(C)C)(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Cl.Cl.[F:52][C:53]1[CH:54]=[C:55]2[C:60](=[CH:61][C:62]=1[F:63])[N:59]=[C:58]([NH:64][CH2:65][CH2:66][NH:67][CH3:68])[CH:57]=[N:56]2>CN(C=O)C>[F:52][C:53]1[CH:54]=[C:55]2[C:60](=[CH:61][C:62]=1[F:63])[N:59]=[C:58]([NH:64][CH2:65][CH2:66][N:67]([CH3:68])[C:14]([C:9]1[N:10]=[C:11]([CH3:13])[S:12][C:8]=1[C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=1)=[O:16])[CH:57]=[N:56]2

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 69145081HCID 69145081, compound

Product 1

HCID 9911963HCID 9911963, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 5-(4-fluoro-phenyl)-2-methyl-thiazole-4-carboxylic acid (50 mg, 0.21 mmol) in DMF (3 ml) was treated sequentially with N,N-diisopropylethylamine (0.20 ml, excess), HATU (79 mg, 0.21 mmol) then after 15 min. N-(6,7-difluoro-quinoxalin-2-yl)-N′-methyl-ethane-1,2-diamine.dihydrochloride, D2 (65 mg, 0.21 mmol). The reaction mixture was stirred at room temperature, under argon for 72 h then partitioned between diethyl ether and water. The organic phase was washed with water (3×), brine, dried (MgSO4) and the solvent removed in vacuo. The residue was triturated with pentane to afford the title compound as a pale yellow powder (38 mg, 40%).

Workup

  1. customthen partitioned between diethyl ether and water
  2. washThe organic phase was washed with water (3×), brine
  3. dry with materialdried (MgSO4)
  4. customthe solvent removed in vacuo
  5. customThe residue was triturated with pentane

Sources & evidence

ORD record
ord-64378bc6554e4956ae414d87d361b425
Source dataset
uspto-grants-2008_12
Patent number
US07468367B2

Reaction notes

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