tert-Butyl (4-aminophenyl)carbamate → HCID 22022165, compound

HRID 1793415Notes

Reaction equation

HRID 1793415 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][CH:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:16][C:17]1[C:26]2[C:21](=[CH:22][C:23]([O:29][CH2:30][CH2:31][CH2:32][N:33]3[CH2:38][CH2:37][O:36][CH2:35][CH2:34]3)=[C:24]([O:27][CH3:28])[CH:25]=2)[N:20]=[CH:19][N:18]=1>C(O)(C)C>[ClH:16].[ClH:16].[C:6]([NH:8][C:9]1[CH:10]=[CH:11][C:12]([NH:15][C:17]2[C:26]3[C:21](=[CH:22][C:23]([O:29][CH2:30][CH2:31][CH2:32][N:33]4[CH2:34][CH2:35][O:36][CH2:37][CH2:38]4)=[C:24]([O:27][CH3:28])[CH:25]=3)[N:20]=[CH:19][N:18]=2)=[CH:13][CH:14]=1)([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7]

Participants

4

Reactant 2

HCID 688611tert-Butyl (4-aminophenyl)carbamateHCID 118239414-Chloro-6-methoxy-7-(3-morpholin-4-ylpropoxy)quinazoline

Product 1

HCID 22022165HCID 22022165, compoundYield 189.4%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of N-(t-butoxycarbonyl) 4-aminoaniline (5.73 g, 27.5 mmol), and 4-chloro-6-methoxy-7-(3-morpholinopropoxy)quinazoline (8.44 g, 25.0 mmol), in isopropanol (100 ml) was heated at reflux for 3.5 hours before the reaction was allowed to cool to ambient temperature. The solid which had precipitated was collected by suction filtration and washed with diethyl ether (2×100 ml). Drying of this material yielded 4-(4-(N-Boc-amino)anilino)-6-methoxy-7-(3-morpholinopropoxy)quinazoline dihydrochloride (13.79 g, 95% yield) as a white solid:

Workup

  1. temperatureat reflux for 3.5 hours before the reaction
  2. customThe solid which had precipitated
  3. filtrationwas collected by suction filtration
  4. washwashed with diethyl ether (2×100 ml)
  5. customDrying of this material

Sources & evidence

ORD record
ord-40883f32ac2e49d894bc6c508a078743
Source dataset
uspto-grants-2006_07
Patent number
US07081461B1

Reaction notes

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