Triethylamine → {[2-(Tert-butoxycarbonyl-methyl-amino)-acetyl]-methyl-amino}-acetic acid 1-{4-[2-(2-hydroxy-phenyl)-7-methyl-quinazolin-4-yl]-piperazine-1-carbonyl}-3-methyl-butyl ester

HRID 2062254Notes

Reaction equation

HRID 2062254 reaction equation
[CH3:1][CH:2]([CH3:31])[CH2:3][CH:4]([O:13][C:14](=[O:30])[CH2:15][N:16]([C:18](=[O:29])[CH2:19][N:20]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH3:21])[CH3:17])[C:5]([N:7]1[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]1)=[O:6].Cl[C:33]1[C:42]2[C:37](=[CH:38][C:39]([CH3:43])=[CH:40][CH:41]=2)[N:36]=[C:35]([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][C:45]=2[OH:50])[N:34]=1.C(N(CC)CC)C>C(Cl)Cl.O>[OH:50][C:45]1[CH:46]=[CH:47][CH:48]=[CH:49][C:44]=1[C:35]1[N:34]=[C:33]([N:10]2[CH2:11][CH2:12][N:7]([C:5]([CH:4]([O:13][C:14](=[O:30])[CH2:15][N:16]([C:18](=[O:29])[CH2:19][N:20]([C:22]([O:24][C:25]([CH3:26])([CH3:28])[CH3:27])=[O:23])[CH3:21])[CH3:17])[CH2:3][CH:2]([CH3:31])[CH3:1])=[O:6])[CH2:8][CH2:9]2)[C:42]2[C:37](=[CH:38][C:39]([CH3:43])=[CH:40][CH:41]=2)[N:36]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 67099091{[2-(Tert-butoxycarbonyl-methyl-amino)-acetyl]-methyl-amino}-acetic acid 3-methyl-1-(piperazine-1-carbonyl)-butyl esterHCID 1361050322-(4-Chloro-7-methylquinazolin-2-yl)-phenol

Product 1

HCID 136366819{[2-(Tert-butoxycarbonyl-methyl-amino)-acetyl]-methyl-amino}-acetic acid 1-{4-[2-(2-hydroxy-phenyl)-7-methyl-quinazolin-4-yl]-piperazine-1-carbonyl}-3-methyl-butyl ester

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

The amine was taken up in 1 mL CH2Cl2 and treated with 2-(4-chloro-7-methyl-quinazolin-2-yl)-phenol (53 mg, 0.19 mmol) and 49 μL of triethylamine, and stirred at room temperature for 3 h. The reaction mixture was diluted with 10 mL of CH2Cl2 and 10 mL of water. The organic layer was separated and dried over Na2SO4, and the solvent was removed under reduced pressure to give {[2-(tert-butoxycarbonyl-methyl-amino)-acetyl]-methyl-amino}-acetic acid 1-{4-[2-(2-hydroxy-phenyl)-7-methyl-quinazolin-4-yl]-piperazine-1-carbonyl}-3-methyl-butyl ester. LC/MS: m/z 677.4 (M+H)+ at 3.25 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

Workup

  1. customThe organic layer was separated
  2. dry with materialdried over Na2SO4
  3. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-89c0186344d042b8afd492682968d10f
Source dataset
uspto-grants-2012_10
Patent number
US08283354B2

Reaction notes

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