HCID 22648102, compound → HCID 22648062, compound

HRID 394124Notes

Reaction equation

HRID 394124 reaction equation
[CH3:1][Mg]Br.[Cl:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]1[CH:20]=[C:19]([C:21](=[O:36])[CH2:22][N:23]2[CH2:28][CH2:27][N:26]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:25][CH2:24]2)[CH:18]=[C:17]2[C:12]=1[CH2:13][N:14]([CH2:46][C:47]1[CH:52]=[CH:51][C:50]([O:53][CH3:54])=[CH:49][CH:48]=1)[C:15](=[O:45])[N:16]2[C:37]1[C:42]([Cl:43])=[CH:41][CH:40]=[CH:39][C:38]=1[Cl:44]>C(Cl)Cl>[Cl:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]1[CH:20]=[C:19]([C:21]([OH:36])([CH3:1])[CH2:22][N:23]2[CH2:28][CH2:27][N:26]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:25][CH2:24]2)[CH:18]=[C:17]2[C:12]=1[CH2:13][N:14]([CH2:46][C:47]1[CH:48]=[CH:49][C:50]([O:53][CH3:54])=[CH:51][CH:52]=1)[C:15](=[O:45])[N:16]2[C:37]1[C:42]([Cl:43])=[CH:41][CH:40]=[CH:39][C:38]=1[Cl:44]

Participants

4

Reactant 2

HCID 22648102HCID 22648102, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 22648062HCID 22648062, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of methylmagnesium bromide (68 μL, 1.4M) in CH2Cl2 (0.2 mL) at 0° C. was added tert-butyl 4-{2-[5-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-3-(4-methoxybenzyl)-2-oxo-1,2,3,4-tetrahydroquinazolin-7-yl]-2-oxoethyl}piperazine-1-carboxylate (EXAMPLE ABA4, Step A) (35.6 mg, 0.047 mmol) dissolved in CH2Cl2 (0.3 mL) slowly. The reaction mixture was stirred for 2 h while warming up to rt. It was quenched with saturated aqueous solution of NH4Cl, and extracted with CH2Cl2. The combined organic layers were washed with brine and dried over Na2SO4. After removal of the solvent, the crude product was purified by preparative thin layer chromatography eluting with 1:3 acetone:hexane to obtain the title compound. Mass spectrum (ESI): 765.2 (M+1).

Workup

  1. customIt was quenched with saturated aqueous solution of NH4Cl
  2. extractionextracted with CH2Cl2
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. customAfter removal of the solvent
  6. customthe crude product was purified by preparative thin layer chromatography
  7. washeluting with 1:3 acetone

Sources & evidence

ORD record
ord-c8d1104dbbb647cc895b434dad5b3c07
Source dataset
uspto-grants-2004_10
Patent number
US06809199B2

Reaction notes

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