Diisopropylethylamine → HCID 59242030, compound

HRID 1876192Notes

Reaction equation

HRID 1876192 reaction equation
[C:1]([O:5][C:6](=[O:26])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([NH:14][C:15]2C3C(=CC=CC=3)N=C(C)N=2)=[CH:10][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:27][C:28]1[NH:37][C:36](=O)[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[N:29]=1.[CH3:39]N([P+](ON1N=NC2C=CC=CC1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)C(C)C)C.C(OC(=O)NC1C=CC(N)=CC=1)(C)(C)C>CN(C=O)C.CCOC(C)=O>[C:1]([O:5][C:6](=[O:26])[N:7]([CH3:39])[C:8]1[CH:9]=[CH:10][C:11]([N:14]([CH3:15])[C:36]2[C:35]3[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=3)[N:29]=[C:28]([CH3:27])[N:37]=2)=[CH:12][CH:13]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

8

Reactant 5

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 688611tert-Butyl (4-aminophenyl)carbamateHCID 68517153HCID 68517153, compoundHCID 1354004572-Methyl-4(3H)-quinazolinone

Product 1

HCID 59242030HCID 59242030, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

[4-(2-Methyl-quinazolin-4-ylamino)-phenyl]-carbamic acid tert-butyl ester: A mixture of 2-methyl-3H-quinazolin-4-one (5 g, 31.2mmol), BOP reagent (16.5 g, 37.4 mmol) and ethyl-diisopropyl-amine (8 mL, 46.8 mmol) in DMF (100 mL) was reacted at ambient temperature for 15 min, followed by treatment with (4-amino-phenyl)-carbamic acid tert-butyl ester (10.7 g, 51.4 mmol). The reaction was run for 24 hours. The reaction mixture was diluted with EtOAc and washed with satd NaHCO3, brine, dried (MgSO4), filtered and concentrated. Isolation was done by MPLC (0-100% EtOAc/hexanes as eluent) to give 1 g of the title compound. 1H NMR (DMSO-d6) δ 8.4-7.6 (8H), 2.6 (s, 3H), 1.5 (s, 9H); LC-MS (ESI+; 351 ([M+H]+)).

Workup

  1. customwas reacted at ambient temperature for 15 min
  2. washwashed with satd NaHCO3, brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-7f091f54c9e74f76835f180fbf2ebc7a
Source dataset
uspto-grants-2012_11
Patent number
US08309562B2

Reaction notes

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