2-Nitrobenzoyl chloride → (4-(2-(3-(Diethylamino)propylamino)quinazolin-4-ylamino)piperidin-1-yl)(2-nitrophenyl)methanone

HRID 215927Notes

Reaction equation

HRID 215927 reaction equation
[CH2:1]([N:3]([CH2:25][CH3:26])[CH2:4][CH2:5][CH2:6][NH:7][C:8]1[N:17]=[C:16]([NH:18][CH:19]2[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]2)[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]=1)[CH3:2].[N+:27]([C:30]1[CH:38]=[CH:37][CH:36]=[CH:35][C:31]=1[C:32](Cl)=[O:33])([O-:29])=[O:28]>C(Cl)Cl.N>[CH2:25]([N:3]([CH2:1][CH3:2])[CH2:4][CH2:5][CH2:6][NH:7][C:8]1[N:17]=[C:16]([NH:18][CH:19]2[CH2:24][CH2:23][N:22]([C:32]([C:31]3[CH:35]=[CH:36][CH:37]=[CH:38][C:30]=3[N+:27]([O-:29])=[O:28])=[O:33])[CH2:21][CH2:20]2)[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]=1)[CH3:26]

Participants

5

Reactant 2

HCID 118752-Nitrobenzoyl chlorideHCID 67027548N2-(3-(diethylamino)propyl)-N4-(piperidin-4-yl)quinazoline-2,4-diamine

Product 1

HCID 67027593(4-(2-(3-(Diethylamino)propylamino)quinazolin-4-ylamino)piperidin-1-yl)(2-nitrophenyl)methanone

Reagents, catalysts & solvents 2

HCID 222AmmoniaSolventHCID 6344DichloromethaneSolvent3×

Procedure

A solution of N2-(3-(diethylamino)propyl)-N4-(piperidin-4-yl)quinazoline-2,4-diamine (55 mg, 0.154 mmol) and 2-nitrobenzoyl chloride (57 mg, 0.309 mmol) and TEA (43 ul, 0.309 mmol) in CH2Cl2 was stirred at room temperature for 1 hour. The crude reaction was directly loaded on the silica gel column and isolated the product using 10% NH3 ca. 7 N MeOH in CH2Cl2 and 90% CH2Cl2 solution as eluent to gain a yellow oil.

Workup

  1. customThe crude reaction
  2. customisolated the product

Sources & evidence

ORD record
ord-a3b150312e5f493fb4ad41ab6eba0682
Source dataset
uspto-grants-2012_06
Patent number
US08193203B2

Reaction notes

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