Ammonia → HCID 60112889, compound

HRID 445165Notes

Reaction equation

HRID 445165 reaction equation
[C:1](Cl)(Cl)=[O:2].[CH3:5][N:6]([CH3:12])[CH2:7][CH2:8][CH2:9][NH:10][CH3:11].C(N(CC)CC)C.[OH:20][C:21]1[CH:51]=[CH:50][C:24]([CH2:25][N:26]2[C:35]3[C:30](=[CH:31][C:32]([O:36][CH2:37][C:38]#[CH:39])=[CH:33][CH:34]=3)[C:29]([C:40]3[CH:45]=[CH:44][C:43]([CH:46]([CH3:48])[CH3:47])=[CH:42][CH:41]=3)=[N:28][C:27]2=[O:49])=[CH:23][CH:22]=1.N.[OH-].[Na+]>C1(C)C=CC=CC=1.ClCCl>[CH:46]([C:43]1[CH:44]=[CH:45][C:40]([C:29]2[C:30]3[C:35](=[CH:34][CH:33]=[C:32]([O:36][CH2:37][C:38]#[CH:39])[CH:31]=3)[N:26]([CH2:25][C:24]3[CH:23]=[CH:22][C:21]([O:20][C:1](=[O:2])[N:10]([CH2:9][CH2:8][CH2:7][N:6]([CH3:12])[CH3:5])[CH3:11])=[CH:51][CH:50]=3)[C:27](=[O:49])[N:28]=2)=[CH:41][CH:42]=1)([CH3:47])[CH3:48]

Participants

9

Reactant 6

HCID 222AmmoniaHCID 6371PhosgeneHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 783021,3-Propanediamine, N1,N1,N3-trimethyl-HCID 60112821HCID 60112821, compound

Product 1

HCID 60112889HCID 60112889, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent2×

Procedure

To an excess of phosgene dissolved in toluene are added at 0° C. 41.5 μl (0.283 mmol) N,N,N′-trimethyl-1,3-propanediamine. After 5 minutes the solvent is evaporated and the residue is dissolved in 2 ml dichloromethane. Triethylamine (79.2 μl, 0.566 mmol) and a solution of 100 mg (0.236 mmol) 1-(4-hydroxy-benzyl)-4-(4-isopropyl-phenyl)-6-prop-2-ynyloxy-1H-quinazolin-2-one in 2 ml dichloromethane are added at 0° C. After stirring for 20 h at rt aqueous ammonia and 0.1 M NaOH are added. The title compound is obtained by extraction with dichloromethane followed by reversed phase preparative HPLC.

Workup

  1. additionare added at 0° C
  2. customAfter 5 minutes the solvent is evaporated
  3. dissolutionthe residue is dissolved in 2 ml dichloromethane
  4. additionare added

Sources & evidence

ORD record
ord-fc17dec741ca4507bcccc0aca0fe05a0
Source dataset
uspto-grants-2013_07
Patent number
US08476286B2

Reaction notes

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