Carbamate → N2-(Azetidin-3-ylmethyl)-N4-(1-(2-(dimethylamino)-6-(2-(dimethylamino)ethoxy)benzyl)piperidin-4-yl)-6,7-dimethoxyquinazoline-2,4-diamine

HRID 215937Notes

Reaction equation

HRID 215937 reaction equation
Cl[C:2]1[N:11]=[C:10]([NH:12][CH:13]2[CH2:18][CH2:17][N:16]([CH2:19][C:20]3[C:25]([O:26][CH2:27][CH2:28][N:29]([CH3:31])[CH3:30])=[CH:24][CH:23]=[CH:22][C:21]=3[N:32]([CH3:34])[CH3:33])[CH2:15][CH2:14]2)[C:9]2[C:4](=[CH:5][C:6]([O:37][CH3:38])=[C:7]([O:35][CH3:36])[CH:8]=2)[N:3]=1.[NH2:39][CH2:40][CH:41]1[CH2:44][N:43](C(OC(C)(C)C)=O)[CH2:42]1.C(=O)([O-])N.C(C(O)=O)(F)(F)F>>[NH:43]1[CH2:44][CH:41]([CH2:40][NH:39][C:2]2[N:11]=[C:10]([NH:12][CH:13]3[CH2:18][CH2:17][N:16]([CH2:19][C:20]4[C:25]([O:26][CH2:27][CH2:28][N:29]([CH3:30])[CH3:31])=[CH:24][CH:23]=[CH:22][C:21]=4[N:32]([CH3:33])[CH3:34])[CH2:15][CH2:14]3)[C:9]3[C:4](=[CH:5][C:6]([O:37][CH3:38])=[C:7]([O:35][CH3:36])[CH:8]=3)[N:3]=2)[CH2:42]1

Participants

5

Reactant 4

HCID 276Carbamate2×HCID 6422Trifluoroacetic acidHCID 10679125Tert-butyl 3-(aminomethyl)azetidine-1-carboxylateHCID 580061992-Chloro-N-(1-(2-(dimethylamino)-6-(2-(dimethylamino)ethoxy)benzyl)piperidin-4-yl)-6,7-dimethoxyquinazolin-4-amine

Product 1

HCID 58006259N2-(Azetidin-3-ylmethyl)-N4-(1-(2-(dimethylamino)-6-(2-(dimethylamino)ethoxy)benzyl)piperidin-4-yl)-6,7-dimethoxyquinazoline-2,4-diamine

Procedure

Following General Procedure D, Compound 75 (100 mg, 0.18 mmol) and tert-butyl 3-(aminomethyl)azetidine-1-carboxylate (62 mg, 0.31 mmol) were converted into the carbamate product. The crude carbamate product was treated with CF3CO2H and purified using neutral alumina prep TLC, eluting with 5% NH3-MeOH and 95% CH2Cl2 to isolate the title compound.

Workup

  1. custompurified
  2. washeluting with 5% NH3-MeOH and 95% CH2Cl2

Sources & evidence

ORD record
ord-05b85d18fbf446a1897f7fbc1dc6c43f
Source dataset
uspto-grants-2012_06
Patent number
US08193203B2

Reaction notes

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