Ammonia → HCID 68695596, compound

HRID 2238419Notes

Reaction equation

HRID 2238419 reaction equation
[Cl:1][CH2:2][CH:3]1[C:11]2[C:10]3[CH:12]=[C:13]([C:16]([OH:18])=O)[CH:14]=[CH:15][C:9]=3[C:8]([N+:19]([O-:21])=[O:20])=[CH:7][C:6]=2[NH:5][CH2:4]1.[CH3:22][N:23]([CH3:27])[CH2:24][CH2:25][NH2:26].C(P(=O)(OCC)OCC)#N.N.[Na+].[Cl-]>CN(C=O)C>[Cl:1][CH2:2][CH:3]1[C:11]2[C:10]3[CH:12]=[C:13]([C:16]([NH:26][CH2:25][CH2:24][N:23]([CH3:27])[CH3:22])=[O:18])[CH:14]=[CH:15][C:9]=3[C:8]([N+:19]([O-:21])=[O:20])=[CH:7][C:6]=2[NH:5][CH2:4]1

Participants

7

Reactant 5

HCID 222AmmoniaHCID 5234Sodium ChlorideHCID 66053N,N-DimethylethylenediamineHCID 76257Diethyl cyanophosphonateHCID 68692459HCID 68692459, compound

Product 1

HCID 68695596HCID 68695596, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A stirred solution of 187 (120 mg, 0.39 mmol) in dry DMF (1.5 mL) was treated at 0° C. with N,N-dimethyl-1,2-ethanediamine (107 μL, 0.97 mmol), followed by the dropwise addition of diethyl cyanophosphonate (128 μL, 93%, 0.78 mmol). The mixture was warmed to room temperature for 45 min, then poured into dilute aqueous NH3 saturated with NaCl. The resulting solid was collected, washed with water and recrystallised twice from CH2Cl2/i-Pr2O to give 1-(chloromethyl)-N-[2-(dimethylamino)ethyl]-5-nitro-1,2-dihydro-3H-benzo[e]indole-8-carboxamide (188) (88 mg, 60%) as a red solid: mp 178-180° C.; 1H NMR [(CD3)2SO] δ 8.68 (t, J=5.7 Hz, 1H), 8.22 (d, J=1.2 Hz, 1H), 8.16 (d, J=9.1 Hz, 1H), 7.77 (dd, J=9.1, 1.7 Hz, 1H), 7.72 (s, 1H), 6.41 (d, J=1.7 Hz, 1H), 4.28-4.18 (m, 1H), 3.98 (dd, J=10.9, 3.7 Hz, 1H), 3.84 (td, J=9.7, 2.4 Hz, 1H), 3.75 (dd, J=−11.0, 9.0 Hz, 2H), 3.49-3.37 (m, 2H), 2.45 (t, J=7.0 Hz, 2H), 2.21 (s, 6H). Anal. (C18H21ClN4O3) C, H, N.

Workup

  1. customThe resulting solid was collected
  2. washwashed with water
  3. customrecrystallised twice from CH2Cl2/i-Pr2O

Sources & evidence

ORD record
ord-b14d10d1f8c0483a98bc27e67523c60c
Source dataset
uspto-grants-2010_05
Patent number
US07718688B2

Reaction notes

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