Diisopropylethylamine → HCID 49779103, compound

HRID 449496Notes

Reaction equation

HRID 449496 reaction equation
F[P-](F)(F)(F)(F)F.C[N+](C)=C(N(C)C)ON1C2N=CC=CC=2N=N1.[NH2:25][C:26]1[N:35]=[C:34]([N:36]2[CH2:41][CH2:40][N:39]([CH3:42])[CH2:38][CH2:37]2)[C:33]2[C:28](=[CH:29][C:30]([C:43]([OH:45])=O)=[CH:31][CH:32]=2)[N:27]=1.C(N(CC)C(C)C)(C)C.[C:55]1([C:69]2[CH:74]=[CH:73][CH:72]=[CH:71][CH:70]=2)[CH:60]=[CH:59][C:58]([CH2:61][CH:62]([C:64]2[S:65][CH:66]=[CH:67][N:68]=2)[NH2:63])=[CH:57][CH:56]=1>CN(C)C=O>[NH2:25][C:26]1[N:35]=[C:34]([N:36]2[CH2:41][CH2:40][N:39]([CH3:42])[CH2:38][CH2:37]2)[C:33]2[C:28](=[CH:29][C:30]([C:43]([NH:63][CH:62]([C:64]3[S:65][CH:66]=[CH:67][N:68]=3)[CH2:61][C:58]3[CH:57]=[CH:56][C:55]([C:69]4[CH:74]=[CH:73][CH:72]=[CH:71][CH:70]=4)=[CH:60][CH:59]=3)=[O:45])=[CH:31][CH:32]=2)[N:27]=1

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 594966492-Amino-4-(4-methylpiperazin-1-yl)quinazoline-7-carboxylic acidHCID 59496766HCID 59496766, compound

Product 1

HCID 49779103HCID 49779103, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N,N,N′,N′-Tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (26 mg, 0.070 mmol) was added to a solution of 2-amino-4-(4-methylpiperazin-1-yl)quinazoline-7-carboxylic acid (10 mg, 0.03 mmol) in N,N-Dimethylformamide (1 mL) and N,N-Diisopropylethylamine (12 uL, 0.070 mmol). The reaction was stirred for 10 min., and the 2-biphenyl-4-yl-1-(1,3-thiazol-2-yl)ethanamine (20 mg, 0.070 mmol) was added. The reaction was stirred for 1 h. at r.t. The final product was purified by prep RP-HPLC (pH=10) to afford the desired compound (0.003 g, 20%) as an amorphous white solid. Analytical LCMS (M+H)+: m/z=550.0.

Workup

  1. stirringThe reaction was stirred for 1 h. at r.t
  2. customThe final product was purified by prep RP-HPLC (pH=10)

Sources & evidence

ORD record
ord-9debc8ecb52f4a7593ee459585b79d14
Source dataset
uspto-grants-2013_07
Patent number
US08481732B2

Reaction notes

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