Hydroxyamine hydrochloride → HCID 58031584, compound

HRID 2067631Notes

Reaction equation

CN(C)/C=C/C(C1SC(N2CCN(CC3C=CC(C(F)(F)F)=CC=3)C2=O)=NC=1C)=O.C[N:32](C)/[C:33](/[CH3:60])=[CH:34]/[C:35]([C:37]1[S:41][C:40]([N:42]2[CH2:46][CH2:45][N:44]([CH2:47][C:48]3[CH:53]=[CH:52][C:51]([C:54]([F:57])([F:56])[F:55])=[CH:50][CH:49]=3)[C:43]2=[O:58])=[N:39][C:38]=1[CH3:59])=[O:36].Cl.NO>>[CH3:59][C:38]1[N:39]=[C:40]([N:42]2[CH2:46][CH2:45][N:44]([CH2:47][C:48]3[CH:53]=[CH:52][C:51]([C:54]([F:57])([F:56])[F:55])=[CH:50][CH:49]=3)[C:43]2=[O:58])[S:41][C:37]=1[C:35]1[O:36][N:32]=[C:33]([CH3:60])[CH:34]=1

Participants

Reactant 3

HCID 443297Hydroxyamine hydrochloride

HCID 58031425HCID 58031425, compound

HCID 58031507HCID 58031507, compound

Product 1

HCID 58031584HCID 58031584, compoundYield 53%

Procedure

Following the procedure as described in Example 38, making variations as required to replace (E)-1-(5-(3-(dimethylamino)acryloyl)-4-methylthiazol-2-yl)-3-(4-(trifluoromethyl)benzyl)imidazolidin-2-one with (E)-1-(5-(3-(dimethylamino)but-2-enoyl)-4-methylthiazol-2-yl)-3-(4-(trifluoromethyl)benzyl)imidazolidin-2-one to react with hydroxylamine hydrochloride, the title compound was obtained as a colorless solid in 53% yield: mp 201-203° C. (ethyl acetate/hexanes); 1H NMR (300 MHz, CDCl3) δ 7.59 (d, J=8.1 Hz, 2H), 7.41 (d, J=8.1 Hz, 2H), 6.07 (s, 1H), 4.54 (s, 2H), 4.12-4.06 (m, 2H), 3.50-3.44 (m, 2H), 2.51 (s, 3H), 2.24 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 163.4, 160.8, 158.2, 155.5, 147.8, 139.8, 130.5, 128.5, 125.9, 122.1, 112.0, 101.0, 47.6, 42.0, 41.9, 17.0, 11.4; MS (ES+) m/z 423.1 (M+1).

Sources & evidence

ORD record: ord-03884c2232bd4154a7889f9a4a4868f5
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08293768B2

Reaction notes

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