Diisopropylethylamine → HCID 49778968, compound

HRID 449514Notes

Reaction equation

HRID 449514 reaction equation
F[P-](F)(F)(F)(F)F.C[N+](C)=C(N(C)C)ON1C2N=CC=CC=2N=N1.[CH3:25][O:26][C:27]1[CH:41]=[CH:40][C:30]([O:31][C:32]2[CH:33]=[C:34]([CH2:38][NH2:39])[CH:35]=[CH:36][CH:37]=2)=[CH:29][CH:28]=1.[NH2:42][C:43]1[N:52]=[C:51]([N:53]2[CH2:58][CH2:57][N:56]([CH3:59])[CH2:55][CH2:54]2)[C:50]2[C:45](=[CH:46][C:47]([C:60](O)=[O:61])=[CH:48][CH:49]=2)[N:44]=1.C(N(CC)C(C)C)(C)C>CN(C)C=O>[NH2:42][C:43]1[N:52]=[C:51]([N:53]2[CH2:54][CH2:55][N:56]([CH3:59])[CH2:57][CH2:58]2)[C:50]2[C:45](=[CH:46][C:47]([C:60]([NH:39][CH2:38][C:34]3[CH:35]=[CH:36][CH:37]=[C:32]([O:31][C:30]4[CH:40]=[CH:41][C:27]([O:26][CH3:25])=[CH:28][CH:29]=4)[CH:33]=3)=[O:61])=[CH:48][CH:49]=2)[N:44]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 3325091HCID 3325091, compoundHCID 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 acid

Product 1

HCID 49778968HCID 49778968, compoundYield 54%

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 crude 1-[3-(4-methoxyphenoxy)phenyl]methanamine (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 (2.0 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 RP-HPLC (pH=10) to give the desired product (0.014 g, 44%) as a white amorphous solid. Analytical LCMS (M+H)+: m/z=499.0.

Workup

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

Sources & evidence

ORD record
ord-d551eb3b3bbe422f88b30587269a104d
Source dataset
uspto-grants-2013_07
Patent number
US08481732B2

Reaction notes

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