Diisopropylethylamine → HCID 86616271, compound

HRID 1788019Notes

Reaction equation

HRID 1788019 reaction equation
[O:1]1[C:5]([C:6]([OH:8])=O)=[CH:4][CH:3]=[N:2]1.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C.[OH:42][S:43]([C:46]([F:49])([F:48])[F:47])(=[O:45])=[O:44].OS(C(F)(F)F)(=O)=O.[C:58]1([N:64]2[CH2:69][CH2:68][N:67]([C:70]3[N:71]=[C:72]([NH:79][CH:80]4[CH2:84][CH2:83][CH2:82][CH:81]4[NH2:85])[C:73]4[S:78][CH2:77][CH2:76][C:74]=4[N:75]=3)[CH2:66][CH2:65]2)[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=1>CN(C)C=O>[OH:45][S:43]([C:46]([F:49])([F:48])[F:47])(=[O:44])=[O:42].[C:58]1([N:64]2[CH2:65][CH2:66][N:67]([C:70]3[N:71]=[C:72]([NH:79][C@H:80]4[CH2:84][CH2:83][CH2:82][C@@H:81]4[NH:85][C:6]([C:5]4[O:1][N:2]=[CH:3][CH:4]=4)=[O:8])[C:73]4[S:78][CH2:77][CH2:76][C:74]=4[N:75]=3)[CH2:68][CH2:69]2)[CH:59]=[CH:60][CH:61]=[CH:62][CH:63]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 20605991,2-Oxazole-5-carboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86616273HCID 86616273, compound

Product 1

HCID 86616271HCID 86616271, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

0.004 g (0.03 mmol) of isoxazole-5-carboxylic acid (IX), 0.012 g (0.03 mmol) of O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluroniumhexafluorophosphate (HATU), and 0.017 mL (0.10 mmol) of diisopropylethylamine are placed in 1 mL of dimethylformamide, stirred for 0.1 hours at ambient temperature. Then 0.020 g (0.03 mmol) of N-[2-(4-phenylpiperazin-1-yl)-6,7-dihydrothieno[3,2-d]pyrimidin-4-yl]cyclopentane-1,2-diamine ditriflate (VIII) (chiral) in 1 mL of dimethylformamide are added. The mixture is shaken for 1 hour at ambient temperature. Then the reaction mixture is purified directly by HPLC through an RP column (column: XTerra, MS-C18, 5 μm, 19*100 mm, eluant: water+0.1% trifluoroacetic acid (A), acetonitrile+0.1% trifluoroacetic acid (B)).

Workup

  1. stirringThe mixture is shaken for 1 hour at ambient temperature
  2. customThen the reaction mixture is purified directly by HPLC through an RP column (column: XTerra, MS-C18, 5 μm, 19*100 mm, eluant: water+0.1% trifluoroacetic acid (A), acetonitrile+0.1% trifluoroacetic acid (B))

Sources & evidence

ORD record
ord-90146dd795e145a2aa64a71cc41b97bb
Source dataset
uspto-grants-2009_03
Patent number
US07511045B2

Reaction notes

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