3-(Tert-butoxy)benzoic acid → 3-tert-Butoxy-N-[4-(2-methylsulfanyl-pyrimidin-4-yloxy)-naphthalen-1-yl]-benzamide

HRID 1171370Notes

Reaction equation

HRID 1171370 reaction equation
[C:1]([O:5][C:6]1[CH:7]=[C:8]([CH:12]=[CH:13][CH:14]=1)[C:9]([OH:11])=O)([CH3:4])([CH3:3])[CH3:2].[CH3:15][S:16][C:17]1[N:22]=[C:21]([O:23][C:24]2[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[C:27]([NH2:34])=[CH:26][CH:25]=2)[CH:20]=[CH:19][N:18]=1>>[C:1]([O:5][C:6]1[CH:7]=[C:8]([CH:12]=[CH:13][CH:14]=1)[C:9]([NH:34][C:27]1[C:28]2[C:33](=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:24]([O:23][C:21]2[CH:20]=[CH:19][N:18]=[C:17]([S:16][CH3:15])[N:22]=2)=[CH:25][CH:26]=1)=[O:11])([CH3:2])([CH3:3])[CH3:4]

Participants

3

Reactant 2

HCID 5865983-(Tert-butoxy)benzoic acidHCID 595533854-(2-Methylsulfanylpyrimidin-4-yloxy)-naphthalen-1-ylamine

Product 1

HCID 595532003-tert-Butoxy-N-[4-(2-methylsulfanyl-pyrimidin-4-yloxy)-naphthalen-1-yl]-benzamide

Procedure

Compound is prepared from 3-tert-butoxy-benzoic acid and 4-(2-methylsulfanyl-pyrimidin-4-yloxy)-naphthalen-1-ylamine according to conditions described in general procedure G. (0.130 g) (46%). Mp: 135-136° C. 1H NMR (300 MHz, DMSOd6) 10.49 (s, 1H), 8.56 (d, J=4.2 Hz, 1H), 8.04 (d, J=6.3 Hz, 1H), 7.83 (brd, 2H), 7.68-7.47 (m, 6H), 7.25 (d, J=5.7 Hz, 1H), 6.93 (d, J=4.5 Hz, 1H), 2.27 (s, 3H), 1.36 (s, 9H). MS: 460 (M+1).

Sources & evidence

ORD record
ord-31cddc8641db44c5acf0c855d73d2848
Source dataset
uspto-grants-2010_11
Patent number
US07829560B2

Reaction notes

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