STK598682 → HCID 58930687, compound

HRID 416289Notes

Reaction equation

HRID 416289 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=[O:37])[C:10]1[CH:15]=[CH:14][C:13]([CH2:16]NC2N=C(NCCC3C=CC(OC)=C(OC)C=3)C=CN=2)=[CH:12][CH:11]=1.COC1C=C(CCNC2C=CN=C(NCC3C=CC(C(O)=O)=CC=3)N=2)C=CC=1OC.[O:68]=[C:69]1[NH:73][C:72](=[O:74])[CH:71](CC2C=CC(C(O)=O)=CC=2)[S:70]1>>[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=[O:37])[C:10]1[CH:11]=[CH:12][C:13]([CH2:16][CH:71]2[S:70][C:69](=[O:68])[NH:73][C:72]2=[O:74])=[CH:14][CH:15]=1

Participants

4

Reactant 3

HCID 4097443STK598682HCID 66622042HCID 66622042, compoundHCID 66622459HCID 66622459, compound

Product 1

HCID 58930687HCID 58930687, compoundYield 51%

Procedure

Following the procedure described for the synthesis of compound 10a (scheme 2, Example 2) but replacing acid 9 by the acid 352, title compound was obtained in 51% yield. 1H NMR: (400 MHz, DMSO-d6, δ (ppm): 12.04 (br s, 1H), 9.62 (s, 1H), 7.90 (d, j=8.2 Hz, 2H), 7.36 (d, J=8.2, 2H), 7.16 (d (dd) J=8.4, 1H), 7.13 (d (dd), J=6.7, 1H), 6.95 (dd, J=1.6 Hz, J=7.8 Hz, 1H), 6.75 (dd, j=1.4 Hz, j=8.0 Hz, 1H), 6.57 (dd, j=1.4 Hz, 7.6 Hz, 1H), 4.99 (dd, J=4.7 Hz, J=9.0 Hz, 1H), 4.96 (br s, 2H), 3.45 (dd, J=4.5 Hz, J=14.1 Hz, 1H), 3.22 (dd, J=9.0 Hz, J=14.3 Hz, 1H). LRMS: 341.3 (calcd.), 342.3 [MH]+ (found).

Sources & evidence

ORD record
ord-91d426abb5b64a49acbc776feb4cd6c5
Source dataset
uspto-grants-2012_01
Patent number
US08088805B2

Reaction notes

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