N-(6-Aminohexyl)-1-naphthalenesulfonamide → Naphthalene-1-sulfonic acid [6-(4-amino-quinazolin-2-ylamino)-hexyl]-amide

HRID 429016

Reaction equation

HRID 429016 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][NH:8][S:9]([C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][CH:13]=1)(=[O:11])=[O:10].Cl[C:23]1[N:32]=[C:31]([NH2:33])[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[N:24]=1>C(O)CC(C)C>[NH2:33][C:31]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[N:24]=[C:23]([NH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][NH:8][S:9]([C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:15]=[CH:14][CH:13]=2)(=[O:11])=[O:10])[N:32]=1

Participants

4

Reactant 2

HCID 4314N-(6-Aminohexyl)-1-naphthalenesulfonamideHCID 2528792-Chloroquinazolin-4-amine

Product 1

HCID 9955360Naphthalene-1-sulfonic acid [6-(4-amino-quinazolin-2-ylamino)-hexyl]-amide

Reagents, catalysts & solvents 1

HCID 31260Isoamyl AlcoholSolvent

Procedure

A solution of naphthalene-1-sulfonic acid (6-amino-hexyl)-amide (0.450 g) and 2-chloro-quinazolin-4-ylamine (see: U.S. Pat. No. 3,956,495) (0.264 g) in 20 ml of isopentylalcohol is heated up to 120° C. for 15 h. Concentration of the reaction mixture followed by chromatography on silica gel (B1) yields naphthalene-1-sulfonic acid [6-(4-amino-quinazolin-2-ylamino)-hexyl]-amide as a white powder, melting at 98-101° C. Rf(B1) 0.28, FAB-MS: (M+H)+=450. Ananlytical C26H29N5O2S+HCl+H2O+0.6 1,4 dioxane. m.p. 98-101° C.

Sources & evidence

ORD record
ord-3bf2e74d1a1047269b7eff937a5d4f99
Source dataset
uspto-grants-2001_11
Patent number
US06316203B1

Linked notes

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