Methylamine → HCID 59199291, compound

HRID 2079653Notes

Reaction equation

HRID 2079653 reaction equation
C[C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12](O)=[O:13])=[CH:9][CH:10]=2)[N:5]=[C:4]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([S:22](=[O:25])(=[O:24])[NH2:23])=[CH:18][CH:17]=2)[N:3]=1.CN.C[CH2:29][N:30](C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>>[CH3:29][NH:30][C:12]([C:8]1[CH:7]=[C:6]2[C:11]([CH:2]=[N:3][C:4]([NH:15][C:16]3[CH:17]=[CH:18][C:19]([S:22](=[O:25])(=[O:24])[NH2:23])=[CH:20][CH:21]=3)=[N:5]2)=[CH:10][CH:9]=1)=[O:13]

Participants

5

Reactant 4

HCID 6329MethylamineHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67080801HCID 67080801, compound

Product 1

HCID 59199291HCID 59199291, compoundYield 50%

Procedure

To methyl 2-(4-sulfamoylphenylamino)quinazolin-7-carboxylic acid (1 eq) was added methylamine (2 eq) and DIEA (4 eq) and HBTU (2 eq) and the mixture was stirred at RT overnight. The coupling went to completion and the mixture was concentrated and partitioned between ethyl acetate and water. The organic layers were concentrated and purified on the prep HPLC to give N-methyl-2-(4-sulfamoylphenylamino)quinazoline-7-carboxamide in 50% yield. ES/MS m/z 358 (MH+).

Workup

  1. concentrationthe mixture was concentrated
  2. custompartitioned between ethyl acetate and water
  3. concentrationThe organic layers were concentrated
  4. custompurified on the prep HPLC

Sources & evidence

ORD record
ord-20ac7a22ecbe4300a842cfc04a2bf5b2
Source dataset
uspto-grants-2011_04
Patent number
US07932262B2

Reaction notes

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