Ethyl 4-chloroacetoacetate → HCID 86624685, compound

HRID 604890Notes

Reaction equation

HRID 604890 reaction equation
Cl[CH2:2][C:3](=O)[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].[CH3:11][O:12][C:13]1[CH:14]=[C:15]([NH:25][C:26]([NH2:28])=[S:27])[CH:16]=[CH:17][C:18]=1[N:19]1[CH:23]=[C:22]([CH3:24])[N:21]=[CH:20]1>>[CH2:8]([O:7][C:5](=[O:6])[CH2:4][C:3]1[N:28]=[C:26]([NH:25][C:15]2[CH:16]=[CH:17][C:18]([N:19]3[CH:23]=[C:22]([CH3:24])[N:21]=[CH:20]3)=[C:13]([O:12][CH3:11])[CH:14]=2)[S:27][CH:2]=1)[CH3:9]

Participants

3

Reactant 2

HCID 69484Ethyl 4-chloroacetoacetateHCID 71650841[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]thiourea

Product 1

HCID 86624685HCID 86624685, compound

Procedure

The title compound was prepared in analogy to example 1 step e) from 56 mg (0.33 mmol) ethyl 4-chloroacetoacetate and 79 mg (0.3 mmol) [3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-thiourea. The crude product was purified through stirring with diethyl ether yielding 115 mg (98%) {2-[3-methoxy-4-(4-methyl-imidazol-1-yl)-phenylamino]-thiazol-4-yl}-acetic acid ethyl ester as an off-white solid. MS ISP (m/e): 373.1 (100) (M+H)+. 1H NMR (DMSO-D6, 250 MHz): δ (ppm)=10.68 (s, 1H), 9.26 (s, 1H), 7.83 (s, 1H), 7.65 (s, 1H), 7.46 (d, 1H), 7.22 n(d, 1H), 6.79 (s, 1H), 4.09 (q, 2H), 3.83 (s, 3H), 3.67 (s, 2H), 2.33 (s, 3H), 1.19 (t, 3H).

Workup

  1. customThe crude product was purified

Sources & evidence

ORD record
ord-c3f6d84a5bea4e70a47edbd87604cbcd
Source dataset
uspto-grants-2011_03
Patent number
US07910740B2

Reaction notes

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