1,4-Benzenediamine, N1,N1-dimethyl-, hydrochloride (1:2) → 1-(4-(Dimethylamino)phenyl)-3-(7-(hydroxyamino)-7-oxoheptyl)urea

HRID 404200Notes

Reaction equation

HRID 404200 reaction equation
CN(C)C1C=CC(CNC(=O)NCCCC([NH:16][OH:17])=O)=CC=1.C1(C)C=CC(S(O)(=O)=[O:29])=CC=1.C(O[C:41](=[O:49])[CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][NH2:48])C1C=CC=CC=1.Cl.Cl.[CH3:52][N:53]([CH3:62])[C:54]1[CH:61]=[CH:60][C:57](CN)=[CH:56][CH:55]=1.Cl.Cl.C[N:66]([CH3:74])C1C=CC(N)=CC=1>>[OH:17][NH:16][C:41](=[O:49])[CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][NH:48][C:74]([NH:66][C:57]1[CH:56]=[CH:55][C:54]([N:53]([CH3:52])[CH3:62])=[CH:61][CH:60]=1)=[O:29]

Participants

5

Reactant 4

HCID 27241661,4-Benzenediamine, N1,N1-dimethyl-, hydrochloride (1:2)HCID 27346334-(aminomethyl)-N,N-dimethylaniline dihydrochlorideHCID 184392197-Amino-heptanoic acid benzyl ester toluene-4-sulfonic acidHCID 575981614-[3-(4-Dimethylamino-benzyl)-ureido]-N-hydroxy-butyramide

Product 1

HCID 115588271-(4-(Dimethylamino)phenyl)-3-(7-(hydroxyamino)-7-oxoheptyl)urea

Procedure

Compound 7 was prepared using the methodology described for the preparation of compound 2, by substituting 4-amino-butyric acid benzyl ester toluene-4-sulfonic acid with 7-amino-heptanoic acid benzyl ester toluene-4-sulfonic acid and 4-dimethylaminobenzylamine dihydrochloride with N,N-dimethyl-benzene-1,4-diamine dihydrochloride. 1H NMR (300 MHz, DMSO-d6) δ (ppm) 10.34 (br, s, 1H), 8.64 (br s, 1H), 7.98 (br s, 1H), 7.17 (d, J=9.0 Hz, 2H), 6.65 (d, J=9.0 Hz, 2H), 5.91 (t, J=5.7 Hz, 1H), 3.03 (dt, J=6.6, 6.0 Hz, 2H), 2.79 (s, 6H), 1.94 (t, J=7.5 Hz, 2H), 1.48 (m, 2H), 1.39 (m, 2H), 1.25 (m, 4H).

Sources & evidence

ORD record
ord-b7806a12c34647fc95ef38b0c5f4b7f1
Source dataset
uspto-grants-2014_06
Patent number
US08748463B2

Reaction notes

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