Ethylenediamine → HCID 28754023, compound

HRID 388414Notes

Reaction equation

HRID 388414 reaction equation
NC1C2C(=CC(OC)=C(OC)C=2)N=C([NH:16][CH2:17][CH2:18][NH:19][S:20]([C:23]2[CH:28]=[CH:27][C:26]([C:29]([CH3:32])([CH3:31])[CH3:30])=[CH:25][CH:24]=2)(=[O:22])=[O:21])N=1.C(N)CN.C(C1C=CC=CC=1S(Cl)(=O)=O)(C)(C)C>CO>[NH2:16][CH2:17][CH2:18][NH:19][S:20]([C:23]1[CH:28]=[CH:27][C:26]([C:29]([CH3:32])([CH3:31])[CH3:30])=[CH:25][CH:24]=1)(=[O:22])=[O:21]

Participants

5

Reactant 3

HCID 3301EthylenediamineHCID 11420558HCID 11420558, compoundHCID 1224716057877-28-8

Product 1

HCID 28754023HCID 28754023, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

General Procedure for the Synthesis of Sulfonamides (Scheme 3). N-[2-(4-Amino-6,7-dimethoxy-quinazolin-2-ylamino)-ethyl]-4-tert-butyl-benzene sulfonamide (41): A mixture of ethylenediamine (0.36 g, 6.0 mmol) and t-butylbenzenesulfonyl chloride (0.464 g, 2.0 mmol) in methanol (15 mL) was stirred for 3 h, concentrated, and purified by silica gel chromatography to yield N-(2-amino-ethyl)-4-t-butyl-benzenesulfonamide. Following the procedure for the synthesis of compound 14, compound 42 was obtained. 1HNMR (DMSO-d6) δ 1.17 (s, 9H), 3.11 (s, 2H), 3.48 (s, 2H), 3.86 (s, 3H), 3.93 (s, 3H), 6.90 (s, 1H), 7.50 (d, J=8.4 Hz, 2H), 7.55 (s, 1H), 7.70 (d, J=8.4 Hz, 2H). HRMS (M+H)+ calcd for C22H30N5O4S 460.2013, found 460.2010. Anal. (C22H29N5O4S.HCl) C, H, N.

Workup

  1. concentrationconcentrated
  2. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-d6b9bedd03894e8f91644a43171893c9
Source dataset
uspto-grants-2013_02
Patent number
US08377948B2

Reaction notes

Loading…