4-Chlorobenzylamine → HCID 66637595, compound

HRID 1094735Notes

Reaction equation

HRID 1094735 reaction equation
[F:1][C:2]1[CH:22]=[CH:21][CH:20]=[CH:19][C:3]=1[CH2:4][N:5]1[C:14](=[O:15])[C:13]2[C:8](=[CH:9][C:10]([C:16]([O-])=[O:17])=[CH:11][CH:12]=2)[N:7]=[CH:6]1.CCN(C(C)C)C(C)C.CN(C(ON1N=N[C:42]2[CH:43]=[CH:44][CH:45]=[N:46][C:41]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[Cl:56][C:57]1C=CC(CN)=C[CH:58]=1>C(Cl)Cl>[Cl:56][C:57]1[CH:58]=[C:44]([CH:43]=[CH:42][CH:41]=1)[CH2:45][NH:46][C:16]([C:10]1[CH:9]=[C:8]2[C:13]([C:14](=[O:15])[N:5]([CH2:4][C:3]3[CH:19]=[CH:20][CH:21]=[CH:22][C:2]=3[F:1])[CH:6]=[N:7]2)=[CH:12][CH:11]=1)=[O:17]

Participants

6

Reactant 4

HCID 660364-ChlorobenzylamineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 131729499HCID 131729499, compound

Product 1

HCID 66637595HCID 66637595, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-(2-flourobenzyl)-4-oxo-3,4-dihydroquinazoline-7-carboylate (65 mg, 0.218 mmol was dissolved in DCM (10 mL) followed by the addition of DIEA (0.1 mL), HATU (100 mg) and 4-chlorobenzylamine (34 mg, 0.239 mmol). The mixture was stirred at RT overnight. The residue was semi-purified by flash chromatography and then further purified by rotary prep TLC using DCM-Ether (1:1) to give the desired product in 65% yield with HPLC purity of ≧95%.

Workup

  1. customfurther purified by rotary prep TLC

Sources & evidence

ORD record
ord-dc4b2dc3012944c185edd26659a85f2f
Source dataset
uspto-grants-2012_03
Patent number
US08133998B2

Reaction notes

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