Diisopropylethylamine → HCID 67059676, compound

HRID 1807757Notes

Reaction equation

HRID 1807757 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:10]2[CH2:15][CH2:14][N:13]([CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:12][CH2:11]2)=[O:9])=[CH:4][C:3]=1[F:23].CCN(C(C)C)C(C)C.ClC(Cl)(O[C:37](=[O:43])OC(Cl)(Cl)Cl)Cl.Cl.[NH2:46][CH2:47][C:48]([CH3:52])([CH3:51])[C:49]#[N:50]>ClCCl>[CH2:16]([N:13]1[CH2:12][CH2:11][N:10]([C:8]([C:5]2[CH:6]=[CH:7][C:2]([NH:1][C:37]([NH:50][CH2:49][C:48]([C:47]#[N:46])([CH3:52])[CH3:51])=[O:43])=[C:3]([F:23])[CH:4]=2)=[O:9])[CH2:15][CH2:14]1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 94429TriphosgeneHCID 67059680HCID 67059680, compoundHCID 866385643-amino-2,2-dimethylpropanenitrile hydrochloride

Product 1

HCID 67059676HCID 67059676, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(4-Amino-3-fluorophenyl)(4-benzylpiperazin-1-yl)methanone and Hunig's base (32.5 mmol, 5.38 mL, 4.21 g) were stirred in dichloromethane. Triphosgene (3.54 mmol, 1.051 g) was added and the reaction stirred at ambient temperature for 30 minutes. 3-Amino-2,2-dimethylpropanenitrile hydrochloride (9.57 mmol, 1.289 g) was added and the reaction stirred for a further 30 minutes. The reaction mixture was washed with water and the organic layer concentrated under reduced pressure. The resulting residue was purified by silica column chromatography (eluant dichloromethane/methanol 0% to 5%) to afford the title compound (1.809 g). MS (ESI) m/z 438.1 [M+H]+

Workup

  1. stirringthe reaction stirred for a further 30 minutes
  2. washThe reaction mixture was washed with water
  3. concentrationthe organic layer concentrated under reduced pressure
  4. customThe resulting residue was purified by silica column chromatography (eluant dichloromethane/methanol 0% to 5%)

Sources & evidence

ORD record
ord-292d029d8b1944c494ded5691a20610b
Source dataset
uspto-grants-2013_01
Patent number
US08357679B2

Reaction notes

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