Diisopropylethylamine → HCID 58071471, compound

HRID 1256011Notes

Reaction equation

HRID 1256011 reaction equation
[Br:1][C:2]1[C:3]([C:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[N:11]([S:18]([C:21]3[CH:27]=[CH:26][C:24]([CH3:25])=[CH:23][CH:22]=3)(=[O:20])=[O:19])[CH:10]=2)=[N:4][C:5](Cl)=[N:6][CH:7]=1.[CH3:28][O:29][C:30]1[CH:36]=[C:35]([N:37]2[CH2:42][CH2:41][CH:40]([N:43]3[CH2:48][CH2:47][N:46]([CH3:49])[CH2:45][CH2:44]3)[CH2:39][CH2:38]2)[CH:34]=[CH:33][C:31]=1[NH2:32].CCN(C(C)C)C(C)C>C(O)CCC>[Br:1][C:2]1[C:3]([C:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[N:11]([S:18]([C:21]3[CH:27]=[CH:26][C:24]([CH3:25])=[CH:23][CH:22]=3)(=[O:20])=[O:19])[CH:10]=2)=[N:4][C:5]([NH:32][C:31]2[CH:33]=[CH:34][C:35]([N:37]3[CH2:42][CH2:41][CH:40]([N:43]4[CH2:44][CH2:45][N:46]([CH3:49])[CH2:47][CH2:48]4)[CH2:39][CH2:38]3)=[CH:36][C:30]=2[O:29][CH3:28])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 457899912-Methoxy-4-(4-(4-methylpiperazin-1-yl)piperidin-1-yl)aniline2×HCID 580715031H-Indole, 3-(5-bromo-2-chloro-4-pyrimidinyl)-1-[(4-methylphenyl)sulfonyl]-2×

Product 1

HCID 58071471HCID 58071471, compoundYield 53.9%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

3-(5-Bromo-2-chloropyrimidin-4-yl)-1-tosyl-1H-indole (INTERMEDIATE 6, 372 mg, 0.83 mmol), 2-methoxy-4-(4-(4-methylpiperazin-1-yl)piperidin-1-yl)aniline (INTERMEDIATE 27, 343 mg, 0.83 mmol), and DIEA (0.145 mL, 0.83 mmol) in n-butanol (4.0 mL) were heated at 170° C. for 3 h. The reaction mixture was concentrated in vacuo and the crude residue was purified by chromatography on silica gel (10% MeOH/1% NH4OH in DCM) to give the title product (320 mg, 53.9%). m/z 718.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe crude residue was purified by chromatography on silica gel (10% MeOH/1% NH4OH in DCM)

Sources & evidence

ORD record
ord-c669990346d5499689af60b433670567
Source dataset
uspto-grants-2013_06
Patent number
US08461170B2

Reaction notes

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