Hydrochloric Acid → 2-[2-amino-4-(1,3-dihydroisoindole-2-carbonyl)quinazolin-6-yl]-N-(2-methylaminoethyl)benzenesulfonamide

HRID 1037691Notes

Reaction equation

HRID 1037691 reaction equation
NC1N=C(C(N2CC3C(=CC=CC=3)C2)=O)C2C(=CC=C(C3C=CC=CC=3S(Cl)(=O)=O)C=2)N=1.NCCN(C)C(=O)OC(C)(C)C.[NH2:45][C:46]1[N:55]=[C:54]([C:56]([N:58]2[CH2:66][C:65]3[C:60](=[CH:61][CH:62]=[CH:63][CH:64]=3)[CH2:59]2)=[O:57])[C:53]2[C:48](=[CH:49][CH:50]=[C:51]([C:67]3[CH:72]=[CH:71][CH:70]=[CH:69][C:68]=3[S:73]([NH:76][CH2:77][CH2:78][N:79](C)[C:80](=O)OC(C)(C)C)(=[O:75])=[O:74])[CH:52]=2)[N:47]=1.Cl>O1CCOCC1>[NH2:45][C:46]1[N:55]=[C:54]([C:56]([N:58]2[CH2:66][C:65]3[C:60](=[CH:61][CH:62]=[CH:63][CH:64]=3)[CH2:59]2)=[O:57])[C:53]2[C:48](=[CH:49][CH:50]=[C:51]([C:67]3[CH:72]=[CH:71][CH:70]=[CH:69][C:68]=3[S:73]([NH:76][CH2:77][CH2:78][NH:79][CH3:80])(=[O:74])=[O:75])[CH:52]=2)[N:47]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 2756424N-Boc-N-methylethylenediamineHCID 584571942-[2-Amino-4-(1,3-dihydroisoindole-2-carbonyl)quinazolin-6-yl]benzenesulfonyl chlorideHCID 67433857Tert-butyl (2-{2-[2-amino-4-(1,3-dihydroisoindole-2-carbonyl)quinazolin-6-yl]benzenesulfonylamino}ethyl)methylcarbamate

Product 1

HCID 467019522-[2-amino-4-(1,3-dihydroisoindole-2-carbonyl)quinazolin-6-yl]-N-(2-methylaminoethyl)benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

The product is obtained analogously to the preparation of “A64” by reaction of 2-[2-amino-4-(1,3-dihydroisoindole-2-carbonyl)quinazolin-6-yl]benzenesulfonyl chloride and tert-butyl (2-aminoethyl)methylcarbamate. The resultant tert-butyl (2-{2-[2-amino-4-(1,3-dihydroisoindole-2-carbonyl)quinazolin-6-yl]benzenesulfonylamino}ethyl)methylcarbamate is treated directly with 1 M HCl in dioxane, causing the protecting group to be cleaved. The purification is carried out by means of preparative column chromatography.

Workup

  1. customThe product is obtained analogously to the preparation of “A64”
  2. customThe purification

Sources & evidence

ORD record
ord-cf1e41f6ebec40d1885000ee06dcd2f2
Source dataset
uspto-grants-2013_10
Patent number
US08546565B2

Reaction notes

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