Acetic Acid → HCID 59199256, compound

HRID 2079672Notes

Reaction equation

HRID 2079672 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[N:7][C:8]([NH:12][C:13]3[CH:18]=[CH:17][C:16]([S:19]([NH2:22])(=[O:21])=[O:20])=[CH:15][CH:14]=3)=[N:9]2)=[CH:4][CH:3]=1.[C:23](O)(=[O:25])[CH3:24].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>C1COCC1.C(OCC)(=O)C>[S:19]([C:16]1[CH:15]=[CH:14][C:13]([NH:12][C:8]2[N:7]=[CH:6][C:5]3[C:10](=[CH:11][C:2]([NH:1][C:23](=[O:25])[CH3:24])=[CH:3][CH:4]=3)[N:9]=2)=[CH:18][CH:17]=1)(=[O:21])(=[O:20])[NH2:22]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 59199243HCID 59199243, compound

Product 1

HCID 59199256HCID 59199256, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-(7-aminoquinazolin-2-ylamino]-benzenesulfonamide (1 eq) (For synthesis see example 43) in THF was added acetic acid (5 eq), HBTU (4 eq) and DIEA (10 eq). The reaction mixture was stirred at room temperature for 48 h. The reaction does not go to completion. Diluted with ethyl acetate and washed with water, brine and dried over sodium sulfate. Filtered, concentrated and purified by semi-prep HPLC to provide N-(2-(4-sulfamoylphenylamino) quinazolin-7-yl)acetamide ES/MS m/z 358.0 (MH+).

Workup

  1. washwashed with water, brine
  2. dry with materialdried over sodium sulfate
  3. filtrationFiltered
  4. concentrationconcentrated
  5. custompurified by semi-prep HPLC

Sources & evidence

ORD record
ord-7b229c5e30804bfd886ea17978eb8d0d
Source dataset
uspto-grants-2011_04
Patent number
US07932262B2

Reaction notes

Loading…