Diisopropylethylamine → (S)-2-amino-N-(1-(dimethylamino)-3-(4-isopropoxyphenyl)-1-oxopropan-2-yl)-4-(4-methylpiperazin-1-yl)quinazoline-7-carboxamide

HRID 449478Notes

Reaction equation

HRID 449478 reaction equation
F[P-](F)(F)(F)(F)F.C[N+](C)=C(N(C)C)ON1C2N=CC=CC=2N=N1.[NH2:25][C:26]1[N:35]=[C:34]([N:36]2[CH2:41][CH2:40][N:39]([CH3:42])[CH2:38][CH2:37]2)[C:33]2[C:28](=[CH:29][C:30]([C:43](O)=[O:44])=[CH:31][CH:32]=2)[N:27]=1.C(N(CC)C(C)C)(C)C.[NH2:55][C@@H:56]([CH2:62][C:63]1[CH:68]=[CH:67][C:66]([O:69][CH:70]([CH3:72])[CH3:71])=[CH:65][CH:64]=1)[C:57]([N:59]([CH3:61])[CH3:60])=[O:58]>CN(C)C=O>[NH2:25][C:26]1[N:35]=[C:34]([N:36]2[CH2:37][CH2:38][N:39]([CH3:42])[CH2:40][CH2:41]2)[C:33]2[C:28](=[CH:29][C:30]([C:43]([NH:55][C@@H:56]([CH2:62][C:63]3[CH:64]=[CH:65][C:66]([O:69][CH:70]([CH3:72])[CH3:71])=[CH:67][CH:68]=3)[C:57]([N:59]([CH3:60])[CH3:61])=[O:58])=[O:44])=[CH:31][CH:32]=2)[N:27]=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 59496749(2S)-2-amino-3-(4-isopropoxyphenyl)-N,N-dimethylpropanamide

Product 1

HCID 49779971(S)-2-amino-N-(1-(dimethylamino)-3-(4-isopropoxyphenyl)-1-oxopropan-2-yl)-4-(4-methylpiperazin-1-yl)quinazoline-7-carboxamideYield 20%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N,N,N′,N′-Tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (42 mg, 0.11 mmol) was added to a solution of 2-amino-4-(4-methylpiperazin-1-yl)quinazoline-7-carboxylic acid (20 mg, 0.07 mmol) in N,N-dimethylformamide (2 mL) and N,N-diisopropylethylamine (24 uL, 0.14 mmol). The reaction was stirred for 10 min, and the (2S)-2-amino-3-(4-isopropoxyphenyl)-N,N-dimethylpropanamide (35 mg, 0.14 mmol) was added. The reaction was stirred for 2 h. at r.t., and was purified by RP-HPLC (pH=2) to afford the desired product (7 mg, 20%) as a white solid TFA salt. Analytical LCMS (M+H)+: m/z=520.0.

Workup

  1. stirringThe reaction was stirred for 2 h. at r.t.
  2. customwas purified by RP-HPLC (pH=2)

Sources & evidence

ORD record
ord-e1c537d695a342dc856cc47e43d70f89
Source dataset
uspto-grants-2013_07
Patent number
US08481732B2

Reaction notes

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