2-Chloro-6,7-dimethoxy-4-quinazolinamine → HCID 86701438, compound

HRID 2173903Notes

Reaction equation

HRID 2173903 reaction equation
Cl[C:2]1[N:11]=[C:10]([NH2:12])[C:9]2[C:4](=[CH:5][C:6]([O:15][CH3:16])=[C:7]([O:13][CH3:14])[CH:8]=2)[N:3]=1.[CH2:17]([O:24][C:25]([NH:27][CH2:28][CH2:29][O:30][C:31]1[CH:32]=[C:33]([CH:37]2[NH:42][CH2:41][CH2:40][N:39]([C:43]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44])[CH2:38]2)[CH:34]=[CH:35][CH:36]=1)=[O:26])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C(O)CC(C)C>[NH2:12][C:10]1[C:9]2[C:4](=[CH:5][C:6]([O:15][CH3:16])=[C:7]([O:13][CH3:14])[CH:8]=2)[N:3]=[C:2]([N:42]2[CH2:41][CH2:40][N:39]([C:43]([O:45][C:46]([CH3:49])([CH3:47])[CH3:48])=[O:44])[CH2:38][CH:37]2[C:33]2[CH:34]=[CH:35][CH:36]=[C:31]([O:30][CH2:29][CH2:28][NH:27][C:25]([O:24][CH2:17][C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)=[O:26])[CH:32]=2)[N:11]=1

Participants

4

Reactant 2

HCID 902352-Chloro-6,7-dimethoxy-4-quinazolinamineHCID 86701437HCID 86701437, compound

Product 1

HCID 86701438HCID 86701438, compound

Reagents, catalysts & solvents 1

HCID 31260Isoamyl AlcoholSolvent

Procedure

A solution of 2-chloro-6,7-dimethoxyquinazolin-4-amine (CAS#23680-84-4) (105 mg, 0.439 mmol) and (+) or (−)-tert-butyl 3-(3-(2-(((benzyloxy)carbonyl)amino)ethoxy)phenyl)piperazine-1-carboxylate (100 mg, 0.220 mmol) in isoamyl alcohol (5 ml) was stirred for 16 hr at 135° C. After evaporation, the crude was purified by preparative HPLC (Macherey-Nagel Nucleosil® 100-10 C18, CH3CN/H2O (0.1% TFA)) to give the title compound. MS (ESI+) m/z 659.2 (M+H).

Workup

  1. customAfter evaporation
  2. customthe crude was purified by preparative HPLC (Macherey-Nagel Nucleosil® 100-10 C18, CH3CN/H2O (0.1% TFA))

Sources & evidence

ORD record
ord-c0e1176a484f408caf718f806a060682
Source dataset
uspto-grants-2015_06
Patent number
US09056874B2

Reaction notes

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