Diisopropylethylamine → HCID 49778964, compound

HRID 449492Notes

Reaction equation

HRID 449492 reaction equation
[NH2:1][CH:2]([CH2:8][C:9]1[S:10][C:11]2[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=2[N:13]=1)[C:3]([N:5]([CH3:7])[CH3:6])=[O:4].[NH2:18][C:19]1[N:28]=[C:27]([N:29]2[CH2:34][CH2:33][N:32]([CH3:35])[CH2:31][CH2:30]2)[C:26]2[C:21](=[CH:22][C:23]([C:36](O)=[O:37])=[CH:24][CH:25]=2)[N:20]=1.C(N(CC)C(C)C)(C)C>CN(C)C=O>[NH2:18][C:19]1[N:28]=[C:27]([N:29]2[CH2:30][CH2:31][N:32]([CH3:35])[CH2:33][CH2:34]2)[C:26]2[C:21](=[CH:22][C:23]([C:36]([NH:1][CH:2]([CH2:8][C:9]3[S:10][C:11]4[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=4[N:13]=3)[C:3]([N:5]([CH3:6])[CH3:7])=[O:4])=[O:37])=[CH:24][CH:25]=2)[N:20]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 594966492-Amino-4-(4-methylpiperazin-1-yl)quinazoline-7-carboxylic acidHCID 59496739HCID 59496739, compound

Product 1

HCID 49778964HCID 49778964, compoundYield 49.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-amino-3-(benzo[d]thiazol-2-yl)-N,N-dimethylpropanamide (12.1 mg, 52.2 μmol), 2-amino-4-(4-methylpiperazin-1-yl)quinazoline-7-carboxylic acid (10 mg, 34.8 μmol) from Example 21 Step 4, N,N,N′,N′-tetramethyl-o-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (21.2 mg, 55.7 μmol), N,N-dimethylformamide (2 mL) and N,N-diisopropylethylamine (12.1 μl, 69.6 μmol) was stirred at 25° C. for 60 min The reaction was purified by prep RP-HPLC (pH=10) to afford the desired compound (0.009 g, 49%) as an amorphous white solid. Analytical LCMS (M+H)+: m/z=519.0.

Workup

  1. customwas purified by prep RP-HPLC (pH=10)

Sources & evidence

ORD record
ord-e62a20dc6de1439b968c3df8e48df198
Source dataset
uspto-grants-2013_07
Patent number
US08481732B2

Reaction notes

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