N-methoxy-N-methyl-5-phenylfuran-2-carboxamide → (R)-N-methoxy-N-methyl-2-(1-(phenylsulfonyl)-1H-indol-5-yl)-4,5-dihydrothiazole-4-carboxamide

HRID 522578Notes

Reaction equation

HRID 522578 reaction equation
[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[CH:14][C:15]([C:19]4[S:20][CH2:21][C@@H:22]([C:24](O)=[O:25])[N:23]=4)=[CH:16][CH:17]=3)[CH:12]=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:27][O:28][N:29](C)[C:30](C1OC(C2C=CC=CC=2)=CC=1)=O>>[CH3:27][O:28][N:29]([CH3:30])[C:24]([C@@H:22]1[CH2:21][S:20][C:19]([C:15]2[CH:14]=[C:13]3[C:18](=[CH:17][CH:16]=2)[N:10]([S:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)(=[O:9])=[O:8])[CH:11]=[CH:12]3)=[N:23]1)=[O:25]

Participants

3

Reactant 2

HCID 17832042N-methoxy-N-methyl-5-phenylfuran-2-carboxamideHCID 53363878(R)-2-(1-(Phenylsulfonyl)-1H-indol-5-yl)-4,5-dihydrothiazole-4-carboxylic acid

Product 1

HCID 53363879(R)-N-methoxy-N-methyl-2-(1-(phenylsulfonyl)-1H-indol-5-yl)-4,5-dihydrothiazole-4-carboxamideYield 57.1%

Procedure

(R)—N-methoxy-N-methyl-2-(1-(phenylsulfonyl)-1H-indol-5-yl)-4,5-dihydrothiazole-4-carboxamide (65a) was prepared from 64a with the same method as used for 38d. 57.1% yield. 1H NMR (500 MHz, CDCl3) δ 7.92 (m, 2H), 7.77 (m, 3H), 7.51 (d, 1H, J=3.0 Hz), 7.46 (t, 1H), 7.35 (t, 1H), 6.61 (d, 1H), 5.58 (br, t, 1H) 3.82 (s, 3H), 3.73 (t, 1H), 3.43 (m, 1H), 3.21 (s, 3H). MS (ESI) m/z 452.1 (M+Na)+.

Sources & evidence

ORD record
ord-09e79199aaa8463da092716111039776
Source dataset
uspto-grants-2016_05
Patent number
US09334242B2

Reaction notes

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