Diisopropylethylamine → HCID 59496617, compound

HRID 449508Notes

Reaction equation

HRID 449508 reaction equation
F[P-](F)(F)(F)(F)F.C[N+](C)=C(N(C)C)ON1C2N=CC=CC=2N=N1.Cl.[NH2:26][CH:27]([C:46]([N:48]([CH3:50])[CH3:49])=[O:47])[CH2:28][C:29]1[CH:30]=[C:31]([CH:43]=[CH:44][CH:45]=1)[O:32][C:33]1[CH:42]=[CH:41][C:36]([C:37]([O:39][CH3:40])=[O:38])=[CH:35][CH:34]=1.[NH2:51][C:52]1[N:61]=[C:60]([N:62]2[CH2:67][CH2:66][N:65]([CH3:68])[CH2:64][CH2:63]2)[C:59]2[C:54](=[CH:55][C:56]([C:69](O)=[O:70])=[CH:57][CH:58]=2)[N:53]=1.C(N(CC)C(C)C)(C)C>CN(C)C=O>[NH2:51][C:52]1[N:61]=[C:60]([N:62]2[CH2:63][CH2:64][N:65]([CH3:68])[CH2:66][CH2:67]2)[C:59]2[C:54](=[CH:55][C:56]([C:69]([NH:26][CH:27]([C:46]([N:48]([CH3:50])[CH3:49])=[O:47])[CH2:28][C:29]3[CH:30]=[C:31]([CH:43]=[CH:44][CH:45]=3)[O:32][C:33]3[CH:42]=[CH:41][C:36]([C:37]([O:39][CH3:40])=[O:38])=[CH:35][CH:34]=3)=[O:70])=[CH:57][CH:58]=2)[N:53]=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 67541350HCID 67541350, compound

Product 1

HCID 59496617HCID 59496617, compound

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 methyl 4-{3-[2-amino-3-(dimethylamino)-3-oxopropyl]phenoxy}benzoate 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 with out workup by HPLC (pH=10) to give the desired(0.012 g, 37%) as a white amorphous solid. 1H NMR (400 MHz, DMSO): δ 8.82 (d, 1H), 7.71 (d, 2H), 7.68 (d, 1H), 7.61 (d, 1H), 7.29 (m, 2H), 7.17 (d, 1H), 7.06 (s, 1H), 6.88 (d, 1H), 6.82 (d, 2H), 6.38 (s, 1H), 5.02 (m, 1H), 3.72 (s, 3H), 3.46 (bs, 4H), 3.27 (s, 4H), 2.98 (bs, 5H), 2.77 (s, 3H), 2.17 (s, 3H). Analytical LCMS (M+H)+: m/z=612.0.

Workup

  1. customThe product was purified with out workup by HPLC (pH=10)
  2. customto give the

Sources & evidence

ORD record
ord-c6d31aea38b34dcfb73559593f3817cd
Source dataset
uspto-grants-2013_07
Patent number
US08481732B2

Reaction notes

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