Diisopropylethylamine → HCID 49779236, compound

HRID 449527Notes

Reaction equation

HRID 449527 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](O)=[O:53])=[CH:40][CH:41]=2)[N:36]=1.Cl.[NH2:56][CH:57]1[C:66]2[CH:65]=[C:64]([O:67][CH2:68][C:69]3[CH:70]=[C:71]([CH:74]=[CH:75][CH:76]=3)[C:72]#[N:73])[CH:63]=[CH:62][C:61]=2[CH2:60][CH2:59][CH2:58]1>CN(C)C=O>[NH2:34][C:35]1[N:44]=[C:43]([N:45]2[CH2:46][CH2:47][N:48]([CH3:51])[CH2:49][CH2:50]2)[C:42]2[C:37](=[CH:38][C:39]([C:52]([NH:56][CH:57]3[C:66]4[C:61](=[CH:62][CH:63]=[C:64]([O:67][CH2:68][C:69]5[CH:76]=[CH:75][CH:74]=[C:71]([C:72]#[N:73])[CH:70]=5)[CH:65]=4)[CH2:60][CH2:59][CH2:58]3)=[O:53])=[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 67541550HCID 67541550, compound

Product 1

HCID 49779236HCID 49779236, compoundYield 79.1%

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-{[(8-amino-5,6,7,8-tetrahydronaphthalen-2-yl)oxy]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 (0.013 g, 30%) as an amorphous white solid. 1H NMR (400 MHz, DMSO): δ8.84 (d, 1H), 7.77-7.6 (m, 5H), 7.46 (dd, 1H), 7.42 (m, 1H), 6.99 (d, 1H), 6.80 (dd, 1H), 6.74 (m, 1H), 6.36 (bs, 2H), 5.12 (m, 1H), 5.02 (s, 2H), 3.51 (bs, 4H), 3.27 (s, 4H), 2.62 (m, 2H), 2.17 (s, 3H), 1.88 (m, 2H), 1.70 (m, 2H). Analytical LCMS (M+H)+: m/z=548.1.

Workup

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

Sources & evidence

ORD record
ord-7f22df073f4046c38007eb2f66977856
Source dataset
uspto-grants-2013_07
Patent number
US08481732B2

Reaction notes

Loading…