Methyl 2-((3-(5-(benzylcarbamoyl)-4-methylthiazol-2-yl)-2-oxoimidazolidin-1-yl)methyl)benzoate → 2-((3-(5-(Benzylcarbamoyl)-4-methylthiazol-2-yl)-2-oxoimidazolidin-1-yl)methyl)benzoic acid

HRID 560792Notes

Reaction equation

HRID 560792 reaction equation
C(NC(C1SC(N2CCN(CC3C=C(C=CC=3)C(OCC)=O)C2=O)=NC=1C)=O)C1C=CC=CC=1.[CH2:35]([NH:42][C:43]([C:45]1[S:49][C:48]([N:50]2[CH2:54][CH2:53][N:52]([CH2:55][C:56]3[CH:65]=[CH:64][CH:63]=[CH:62][C:57]=3[C:58]([O:60]C)=[O:59])[C:51]2=[O:66])=[N:47][C:46]=1[CH3:67])=[O:44])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>>[CH2:35]([NH:42][C:43]([C:45]1[S:49][C:48]([N:50]2[CH2:54][CH2:53][N:52]([CH2:55][C:56]3[CH:65]=[CH:64][CH:63]=[CH:62][C:57]=3[C:58]([OH:60])=[O:59])[C:51]2=[O:66])=[N:47][C:46]=1[CH3:67])=[O:44])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Participants

3

Reactant 2

HCID 25097441Methyl 2-((3-(5-(benzylcarbamoyl)-4-methylthiazol-2-yl)-2-oxoimidazolidin-1-yl)methyl)benzoateHCID 59481231Ethyl 3-((3-(5-(benzylcarbamoyl)-4-methylthiazol-2-yl)-2-oxoimidazolidin-1-yl)methyl)benzoate

Product 1

HCID 594811722-((3-(5-(Benzylcarbamoyl)-4-methylthiazol-2-yl)-2-oxoimidazolidin-1-yl)methyl)benzoic acidYield 76%

Procedure

Following the procedure as described in Example 25, making variations as required to replace ethyl 3-((3-(5-(benzylcarbamoyl)-4-methylthiazol-2-yl)-2-oxoimidazolidin-1-yl)methyl)benzoate with methyl 2-((3-(5-(benzylcarbamoyl)-4-methylthiazol-2-yl)-2-oxoimidazolidin-1-yl)methyl)benzoate, the title compound was obtained as a colorless solid in 76% yield: mp 153-156° C. (methanol/hexanes); 1H NMR (300 MHz, DMSO-d6) δ 8.49 (t, J=6.0 Hz, 1H), 7.86 (d, J=9.0 Hz, 1H), 7.57-7.51 (m, 1H), 7.40-7.19 (m, 7H), 4.78 (s, 2H), 4.34 (d, J=6.0 Hz, 2H), 4.01 (t, J=9.0 Hz, 2H), 3.50 (t, J=9.0 Hz, 2H), 2.46 (s, 3H); MS (ES+) m/z 451.2 (M+1).

Sources & evidence

ORD record
ord-012eacee763b48fd8e3696ce45f93ee5
Source dataset
uspto-grants-2011_11
Patent number
US08063084B2

Reaction notes

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