Diisopropylethylamine → HCID 67541940, compound

HRID 449522Notes

Reaction equation

HRID 449522 reaction equation
F[P-](F)(F)(F)(F)F.C[N+](C)=C(N(C)C)ON1[C:16]2[N:17]=[CH:18][CH:19]=[CH:20][C:15]=2N=N1.[ClH:25].[NH2:26][CH:27]([C:29]1[CH:30]=[C:31]([CH:42]=[CH:43][CH:44]=1)[O:32][C:33]1C=CC(Cl)=C[C:34]=1[C:35]#N)[CH3:28].[NH2:45][C:46]1[N:55]=[C:54]([N:56]2[CH2:61][CH2:60][N:59]([CH3:62])[CH2:58][CH2:57]2)[C:53]2[C:48](=[CH:49][C:50]([C:63]([OH:65])=O)=[CH:51][CH:52]=2)[N:47]=1.C(N(CC)C(C)C)(C)C>CN(C)C=O>[NH2:45][C:46]1[N:55]=[C:54]([N:56]2[CH2:61][CH2:60][N:59]([CH3:62])[CH2:58][CH2:57]2)[C:53]2[C:48](=[CH:49][C:50]([C:63]([NH:26][CH:27]([C:29]3[CH:44]=[CH:43][CH:42]=[C:31]([O:32][C:33]4[CH:34]=[CH:35][C:19]([CH3:18])=[C:20]([Cl:25])[C:15]=4[C:16]#[N:17])[CH:30]=3)[CH3:28])=[O:65])=[CH:51][CH:52]=2)[N:47]=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 67541695HCID 67541695, compound

Product 1

HCID 67541940HCID 67541940, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N,N,N′,N′-Tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (0.030 g, 0.078 mmol) was added to a solution of 2-[3-(1-aminoethyl)phenoxy]-5-chlorobenzonitrile HCl salt (0.045 g) and 2-amino-4-(4-methylpiperazin-1-yl)quinazoline-7-carboxylic acid (0.015 g, 0.052 mmol) in N,N-dimethylformamide (1.0 mL) with N,N-diisopropylethylamine (0.027 mL, 0.16 mmol) at r.t. The reaction was stirred for 1 h. The product was purified without workup by RH-HPLC (pH=2) to give the desired product (0.005 g, 20%) as a white amorphous solid TFA salt. 1H NMR (400 MHz, DMSO): δ: 9.23 (d, 1H), 8.10 (d, 1H), 8.05 (d, 1H), 7.90 (d, 1H), 7.78 (d, 1H), 7.70, (dd, 1H), 7.43 (m, 1H), 7.30 (d, 1H), 7.21 (m, 1H), 7.04 (dd, 1H), 6.94 (d, 1H), 5.20 (m 1H), 4.58 (m, 2H), 4.10 (m, 2H), 3.70 (m, 2H), 3.05 (m, 2H), 2.83 (s, 3H), 1.49 (d, 3H). Analytical LCMS (M+H)+: m/z=542.0.

Workup

  1. customThe product was purified without workup by RH-HPLC (pH=2)

Sources & evidence

ORD record
ord-c0a356e0ec9640bc823986c0bc2119c4
Source dataset
uspto-grants-2013_07
Patent number
US08481732B2

Reaction notes

Loading…