Diisopropylethylamine → HCID 59496621, compound

HRID 449531Notes

Reaction equation

HRID 449531 reaction equation
F[P-](F)(F)(F)(F)F.C[N+](C)=C(N(C)C)ON1C2N=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C.[NH2:34][C:35]1[N:44]=[C:43]([N:45]2[CH2:50][CH2:49][N:48]([CH3:51])[CH2:47][CH2:46]2)[C:42]2[C:37](=[CH:38][C:39]([C:52]([OH:54])=O)=[CH:40][CH:41]=2)[N:36]=1.Cl.[CH2:56]1[C:65]2[C:60](=[C:61]([O:66][CH2:67][C:68]3[CH:69]=[C:70]([CH:73]=[CH:74][CH:75]=3)[C:71]#[N:72])[CH:62]=[CH:63][CH:64]=2)[CH2:59][CH2:58][NH:57]1>CN(C)C=O>[NH2:34][C:35]1[N:44]=[C:43]([N:45]2[CH2:50][CH2:49][N:48]([CH3:51])[CH2:47][CH2:46]2)[C:42]2[C:37](=[CH:38][C:39]([C:52]([N:57]3[CH2:58][CH2:59][C:60]4[C:65](=[CH:64][CH:63]=[CH:62][C:61]=4[O:66][CH2:67][C:68]4[CH:69]=[C:70]([CH:73]=[CH:74][CH:75]=4)[C:71]#[N:72])[CH2:56]3)=[O:54])=[CH:40][CH:41]=2)[N:36]=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 68792034HCID 68792034, compound

Product 1

HCID 59496621HCID 59496621, compoundYield 93.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N,N,N′,N′-Tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (20 mg, 0.05 mmol) and N,N-diisopropylethylamine (10 uL, 0.07 mmol) were added to a solution of 2-amino-4-(4-methylpiperazin-1-yl)quinazoline-7-carboxylic acid (10 mg, 0.03 mmol) and 3-[(1,2,3,4-tetrahydroisoquinolin-5-yloxy)methyl]benzonitrile HCl salt (30 mg, 0.07 mmol) in N,N-dimethylformamide (1 mL) at r.t. The reaction was stirred for 2 h. and the product was purified without workup by RP-HPLC (pH=10) to afford the desired compound (0.015 g, 33%) as an amorphous white solid. 1H NMR (500 MHz, DMSO): δ 7.79 (s, 1H), 7.71 (m, 2H.), 7.67 (d, 1H), 7.52 (t, 1H), 7.20 (s, 1), 7.05 (t, 1H), 6.96 (d, 1H), 6.83 (d, 1H), 6.70 (bs, 1H.), 6.02 (s, 2H.), 5.10 (s, 2H), 4.61 (m, 2H), 3.54 (m, 4H), 2.96 (s, 4H), 2.74 (m, 2H.), 2.44 (m, 2H.), 2.18 (s, 3H). (NMR sample heated to 90 c); Analytical LCMS (M+H)+: m/z=534.1.

Workup

  1. customthe product was purified without workup by RP-HPLC (pH=10)

Sources & evidence

ORD record
ord-b13f069de831413cbb9acf43a06714b9
Source dataset
uspto-grants-2013_07
Patent number
US08481732B2

Reaction notes

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