N-(6-acetyl-2-chloro-3-methoxyphenyl)-4-cyclopropylthiazole-2-carboxamide → HCID 178487689, compound

HRID 388696Notes

Reaction equation

HRID 388696 reaction equation
[C:1]([C:4]1[C:9]([NH:10][C:11]([C:13]2[S:14][CH:15]=[C:16]([CH:18]3[CH2:20][CH2:19]3)[N:17]=2)=O)=[C:8]([Cl:21])[C:7]([O:22][CH3:23])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].C(C1N=C(C2C=C(O)C3C(=CC(OC)=CC=3)N=2)SC=1)(C)C>>[Cl:21][C:8]1[C:7]([O:22][CH3:23])=[CH:6][CH:5]=[C:4]2[C:9]=1[N:10]=[C:11]([C:13]1[S:14][CH:15]=[C:16]([CH:18]3[CH2:20][CH2:19]3)[N:17]=1)[CH:2]=[C:1]2[OH:3]

Participants

3

Reactant 2

HCID 59434816N-(6-acetyl-2-chloro-3-methoxyphenyl)-4-cyclopropylthiazole-2-carboxamideHCID 178487691HCID 178487691, compound

Product 1

HCID 178487689HCID 178487689, compoundYield 84%

Procedure

Compound 269a was synthesized from compound 268a (3.50 g, 1 eq) as an orange solid in 84% yield, following the procedure as described for compound 218a (80° C. overnight). 1H NMR (CDCl3, 400 MHz): δ (ppm) 1.04-1.07 (m, 4H), 2.13-2.18 (m, 1H), 4.06 (s, 3H), 6.75 (s, 1H), 7.06 (d, J=9.10 Hz, 1H), 7.09 (s, 1H), 8.27 (d, J=9.10 Hz, 1H), 9.92 (br s, 1H); MS (ESI, EI+): m/z=333.13 (MH+).

Sources & evidence

ORD record
ord-a4256e6f8e274f188f37b29ae2d05f83
Source dataset
uspto-grants-2013_02
Patent number
US08377962B2

Reaction notes

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