(Z)-(1S,4R,6S,18R)-18-hydroxy-13-methyl-2,14-dioxo-3,13,15-triaza-tricyclo[13.4.0.0*4,6*]nonadec-7-ene-4-carboxylic acid methyl ester → (1S,4R,6S,18S)-18[6-(4-Methylthiazol-2-yl)-2-(4-trifluoromethylthiazol-2-yl)-pyrimidin-4-yloxy]-13-N-methyl-2,14-dioxo-3,13,15-triazatricyclo[13.4.0.0*4,6*]nonadec-7-ene-4-carboxylic acid methyl ester

HRID 880818Notes

Reaction equation

HRID 880818 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([C:7]2[N:12]=[C:11]([C:13]3[S:14][CH:15]=[C:16]([C:18]([F:21])([F:20])[F:19])[N:17]=3)[N:10]=[C:9]([OH:22])[CH:8]=2)[S:5][CH:6]=1.[CH3:23][O:24][C:25]([C@@:27]12[CH2:45][C@H:44]1[CH:43]=[CH:42][CH2:41][CH2:40][CH2:39][CH2:38][N:37]([CH3:46])[C:36](=[O:47])[N:35]1[C@@H:30]([CH2:31][C@H:32](O)[CH2:33][CH2:34]1)[C:29](=[O:49])[NH:28]2)=[O:26].COC([C@@]12C[C@H]1C=CCCCCN(C)C(=O)N1[C@@H](C[C@H](OC3C4C(=C(C)C(OC)=CC=4)N=C(C4SC=C(C#C)N=4)C=3)CC1)C(=O)N2)=O>>[CH3:23][O:24][C:25]([C@@:27]12[CH2:45][C@H:44]1[CH:43]=[CH:42][CH2:41][CH2:40][CH2:39][CH2:38][N:37]([CH3:46])[C:36](=[O:47])[N:35]1[C@@H:30]([CH2:31][C@@H:32]([O:22][C:9]3[CH:8]=[C:7]([C:4]4[S:5][CH:6]=[C:2]([CH3:1])[N:3]=4)[N:12]=[C:11]([C:13]4[S:14][CH:15]=[C:16]([C:18]([F:21])([F:20])[F:19])[N:17]=4)[N:10]=3)[CH2:33][CH2:34]1)[C:29](=[O:49])[NH:28]2)=[O:26]

Participants

4

Reactant 3

HCID 68495095(Z)-(1S,4R,6S,18R)-18-hydroxy-13-methyl-2,14-dioxo-3,13,15-triaza-tricyclo[13.4.0.0*4,6*]nonadec-7-ene-4-carboxylic acid methyl esterHCID 87472167(Z)-(1S,4R,6S,18R)-18-[2-(4-ethynyl-thiazol-2-yl)-7-methoxy-8-methyl-quinolin-4-yloxy]-13-methyl-2,14-dioxo-3,13,15-triaza-tricyclo[13.4.0.0*4,6*]nonadec-7-ene-4-carboxylic acid methyl esterHCID 178431896HCID 178431896, compound

Product 1

HCID 68501381(1S,4R,6S,18S)-18[6-(4-Methylthiazol-2-yl)-2-(4-trifluoromethylthiazol-2-yl)-pyrimidin-4-yloxy]-13-N-methyl-2,14-dioxo-3,13,15-triazatricyclo[13.4.0.0*4,6*]nonadec-7-ene-4-carboxylic acid methyl esterYield 97%

Procedure

(1S,4R,6S,18S)-18[6-(4-Methylthiazol-2-yl)-2-(4-trifluoromethylthiazol-2-yl)-pyrimidin-4-yloxy]-13-N-methyl-2,14-dioxo-3,13,15-triazatricyclo[13.4.0.0*4,6*]nonadec-7-ene-4-carboxylic acid methyl ester 41b was synthesized from compounds B1 (150 mg, 1.2 eq.) and 36 (44.3 mg, 1 eq), according to the procedure as described for compound 37, as a beige solid in 97% yield. MS (ESI, EI−) m/z=704 (MH−).

Sources & evidence

ORD record
ord-720bd720893d45bc91b855cc186cd6af
Source dataset
uspto-grants-2015_03
Patent number
US08993595B2

Reaction notes

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