(1S,4R,6S,18S)-18[6-(2,5-Dimethylthien-3-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-(2,5-Dimethylthien-3-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 880820Notes

Reaction equation

HRID 880820 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[CH:37]=[C:36]([CH3:38])[S:35][C:34]=4[CH3:39])[N:30]=[C:29]([C:40]4[S:41][CH:42]=[C:43]([C:45]([F:48])([F:47])[F:46])[N:44]=4)[N:28]=3)[CH2:11][CH2:12]1)[C:7](=[O:49])[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>>[CH3:39][C:34]1[S:35][C:36]([CH3:38])=[CH:37][C:33]=1[C:31]1[N:30]=[C:29]([C:40]2[S:41][CH:42]=[C:43]([C:45]([F:46])([F:47])[F:48])[N:44]=2)[N:28]=[C:27]([O:26][C@@H:10]2[CH2:9][C@@H:8]3[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]4[C@:5]([C:3]([OH:4])=[O:2])([NH:6][C:7]3=[O:49])[CH2:23]4)[CH2:12][CH2:11]2)[CH:32]=1

Participants

3

Reactant 2

HCID 68497024(1S,4R,6S,18S)-18[6-(2,5-Dimethylthien-3-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 68496931(1S,4R,6S,18S)-18[6-(2,5-Dimethylthien-3-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 90%

Procedure

(1S,4R,6S,18S)-18[6-(2,5-Dimethylthien-3-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 42v was synthesized from compound 41v (69 mg, 1.0 eq.), according to the procedure as described for compound 38, as a yellow oil in 90% yield. MS (ESI, EI−) m/z=703(MH−).

Sources & evidence

ORD record
ord-edf9bb727bad44bea9c95e08c8b565ee
Source dataset
uspto-grants-2015_03
Patent number
US08993595B2

Reaction notes

Loading…