Diisopropylethylamine → (S)-N1-(4-(diethylamino)-2-(4-((1,2,3,4-tetrahydronaphthalen-1-yl) carbamoyl)pyridin-2-yl)phenyl)-N3-methyl-N3-(2-morpholinoethyl)isophthalamide

HRID 1408183Notes

Reaction equation

HRID 1408183 reaction equation
[CH2:1]([N:3]([CH2:41][CH3:42])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]([C:13]2[CH:14]=[C:15]([CH:19]=[CH:20][CH:21]=2)[C:16]([OH:18])=O)=[O:12])=[C:6]([C:22]2[CH:27]=[C:26]([C:28](=[O:40])[NH:29][C@@H:30]3[C:39]4[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=4)[CH2:33][CH2:32][CH2:31]3)[CH:25]=[CH:24][N:23]=2)[CH:5]=1)[CH3:2].[CH3:43][NH:44][CH2:45][CH2:46][N:47]1[CH2:52][CH2:51][O:50][CH2:49][CH2:48]1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.C(OCC)(=O)C>[CH2:41]([N:3]([CH2:1][CH3:2])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:12])[C:13]2[CH:21]=[CH:20][CH:19]=[C:15]([C:16]([N:44]([CH3:43])[CH2:45][CH2:46][N:47]3[CH2:52][CH2:51][O:50][CH2:49][CH2:48]3)=[O:18])[CH:14]=2)=[C:6]([C:22]2[CH:27]=[C:26]([C:28](=[O:40])[NH:29][C@@H:30]3[C:39]4[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=4)[CH2:33][CH2:32][CH2:31]3)[CH:25]=[CH:24][N:23]=2)[CH:5]=1)[CH3:42]

Participants

7

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 14979282Methyl(2-(morpholin-4-yl)ethyl)amineHCID 66586992(S)-3-((4-(diethylamino)-2-(4-((1,2,3,4-tetrahydronaphthalen-1-yl)carbamoyl)pyridin-2-yl)phenyl)carbamoyl)benzoic acid

Product 1

HCID 66588130(S)-N1-(4-(diethylamino)-2-(4-((1,2,3,4-tetrahydronaphthalen-1-yl) carbamoyl)pyridin-2-yl)phenyl)-N3-methyl-N3-(2-morpholinoethyl)isophthalamideYield 79%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To a mixture of (S)-3-((4-(diethylamino)-2-(4-((1,2,3,4-tetrahydronaphthalen-1-yl)carbamoyl)pyridin-2-yl)phenyl)carbamoyl)benzoic acid (1.81 mmol, 1.15 g), N-methyl-2-morpholinoethanamine (2.17 mmol, 0.313 g) and DIEA (12.67 mmol, 1.64 g) in DMF (5 mL) was added HATU (2.17 mmol, 0.826 g), and the mixture was stirred at 60° C. for 2 h. The reaction mixture was diluted with ethyl acetate, washed with water (2×), brine (1×), dried and concentrated. The residue was purified by column to give a yellow solid (0.98 g, 79%). MS (ESI, m/z) 689.28 [M+H]+.

Workup

  1. washwashed with water (2×), brine (1×)
  2. customdried
  3. concentrationconcentrated
  4. customThe residue was purified by column

Sources & evidence

ORD record
ord-70ce0790e8e44b59bcbdb689c1e31739
Source dataset
uspto-grants-2014_12
Patent number
US08916569B2

Reaction notes

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