(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 → (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

HRID 880819Notes

Reaction equation

HRID 880819 reaction equation
C[O:2][C:3]([C@@:5]12[CH2:23][C@H:22]1[CH:21]=[CH:20][CH2:19][CH2:18][CH2:17][CH2:16][N:15]([CH3:24])[C:14](=[O:25])[N:13]1[C@@H:8]([CH2:9][C@@H:10]([O:26][C:27]3[CH:32]=[C:31]([C:33]4[S:34][CH:35]=[C:36]([CH3:38])[N:37]=4)[N:30]=[C:29]([C:39]4[S:40][CH:41]=[C:42]([C:44]([F:47])([F:46])[F:45])[N:43]=4)[N:28]=3)[CH2:11][CH2:12]1)[C:7](=[O:48])[NH:6]2)=[O:4].C(C1N=C(C2C=C(O[C@H]3C[C@@H]4N(C(=O)N(C)CCCCC=C[C@H]5[C@](C(O)=O)(NC4=O)C5)CC3)C3C(=C(C)C(OC)=CC=3)N=2)SC=1)#C>>[CH3:38][C:36]1[N:37]=[C:33]([C:31]2[N:30]=[C:29]([C:39]3[S:40][CH:41]=[C:42]([C:44]([F:45])([F:46])[F:47])[N:43]=3)[N:28]=[C:27]([O:26][C@@H:10]3[CH2:9][C@@H:8]4[N:13]([C:14](=[O:25])[N:15]([CH3:24])[CH2:16][CH2:17][CH2:18][CH2:19][CH:20]=[CH:21][C@H:22]5[C@:5]([C:3]([OH:4])=[O:2])([NH:6][C:7]4=[O:48])[CH2:23]5)[CH2:12][CH2:11]3)[CH:32]=2)[S:34][CH:35]=1

Participants

3

Reactant 2

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 esterHCID 87472044(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

Product 1

HCID 91281201(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 acidYield 82%

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 42b was synthesized from compound 41b (250 mg, 1.0 eq.), according to the procedure as described for compound 38, as a green foam in 82% yield. MS (ESI, EI−) m/z=690 (MH−).

Sources & evidence

ORD record
ord-aab1fc8343614aa9bf29842bbac1bfac
Source dataset
uspto-grants-2015_03
Patent number
US08993595B2

Reaction notes

Loading…