4-Fluorophenyl isocyanate → HCID 44514482, compound

HRID 536800Notes

Reaction equation

HRID 536800 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[C:12]([N:14]3[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)[N:11]=[C:10]([NH:20][CH:21]3[CH2:24][N:23]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:22]3)[N:9]=2)=[CH:4][CH:3]=1.[F:32][C:33]1[CH:38]=[CH:37][C:36]([N:39]=[C:40]=[O:41])=[CH:35][CH:34]=1>CN(C1C=CN=CC=1)C>[F:32][C:33]1[CH:38]=[CH:37][C:36]([NH:39][C:40]([NH:1][C:2]2[CH:7]=[CH:6][C:5]([C:8]3[N:13]=[C:12]([N:14]4[CH2:19][CH2:18][O:17][CH2:16][CH2:15]4)[N:11]=[C:10]([NH:20][CH:21]4[CH2:24][N:23]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:22]4)[N:9]=3)=[CH:4][CH:3]=2)=[O:41])=[CH:35][CH:34]=1

Participants

4

Reactant 2

HCID 709554-Fluorophenyl isocyanateHCID 67021834HCID 67021834, compound

Product 1

HCID 44514482HCID 44514482, compound

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

A mixture of tert-butyl 3-{[4-(4-aminophenyl)-6-morpholin-4-yl-1,3,5-triazin-2-yl]amino}azetidine-1-carboxylate (100 mg, 0.23 mmol), 4-fluorophenylisocyanate (63 mg, 0.46 mmol) and DMAP (5 mg) was stirred at room temperature for a period of 24 hours. At the end, reaction mixture was concentrated and purified by Gilson HPLC, using ACN/water and TFA. White solid; Yield 40 mg (30%); (M+H) 565.6

Workup

  1. customAt the end, reaction mixture
  2. concentrationwas concentrated
  3. custompurified by Gilson HPLC

Sources & evidence

ORD record
ord-eb672c30a64c46dcb904e96d65483c68
Source dataset
uspto-grants-2014_10
Patent number
US08859542B2

Reaction notes

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