Dimethyl Ether → HCID 72578579, compound

HRID 2373788Notes

Reaction equation

HRID 2373788 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([CH:22]=[CH:23][C:24]=1[F:25])[O:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH:14]([NH2:21])[C:15]2[O:19][N:18]=[C:17]([CH3:20])[N:16]=2)=[CH:9][CH:8]=1.C(O[C:31](=[O:56])[NH:32][CH:33]([C:50]1[O:54][N:53]=[C:52]([CH3:55])[N:51]=1)[CH2:34][C:35]1[CH:40]=[CH:39][C:38]([O:41][C:42]2[CH:47]=[CH:46][C:45]([F:48])=[C:44]([Cl:49])[CH:43]=2)=[CH:37][CH:36]=1)(C)(C)C.[Cl:57][C:58]1[C:59]([O:77][CH3:78])=[C:60]([C:74](O)=[O:75])[CH:61]=[C:62]([C:64]2[CH:69]=[CH:68][C:67]([C:70]([F:73])([F:72])[F:71])=[CH:66][CH:65]=2)[CH:63]=1.COC>>[Cl:2][C:3]1[CH:4]=[C:5]([CH:22]=[CH:23][C:24]=1[F:25])[O:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH:14]([NH:21][C:74]([C:60]2[CH:61]=[C:62]([C:64]3[CH:65]=[CH:66][C:67]([C:70]([F:72])([F:73])[F:71])=[CH:68][CH:69]=3)[CH:63]=[C:58]([Cl:57])[C:59]=2[O:77][CH3:78])=[O:75])[C:15]2[O:19][N:18]=[C:17]([CH3:20])[N:16]=2)=[CH:9][CH:8]=1.[Cl:49][C:44]1[CH:43]=[C:42]([CH:47]=[CH:46][C:45]=1[F:48])[O:41][C:38]1[CH:39]=[CH:40][C:35]([CH2:34][CH:33]([NH:32][C:31]([C:60]2[CH:61]=[C:62]([C:64]3[CH:65]=[CH:66][C:67]([C:70]([F:73])([F:71])[F:72])=[CH:68][CH:69]=3)[CH:63]=[C:58]([Cl:57])[C:59]=2[OH:77])=[O:56])[C:50]2[O:54][N:53]=[C:52]([CH3:55])[N:51]=2)=[CH:36][CH:37]=1

Participants

6

Reactant 4

HCID 8254Dimethyl EtherHCID 69205100HCID 69205100, compoundHCID 69207935HCID 69207935, compoundHCID 69207979HCID 69207979, compound

Product 2

HCID 72578579HCID 72578579, compoundHCID 86597137HCID 86597137, compound

Procedure

5-Chloro-4-methoxy-4′-trifluoromethyl-biphenyl-3-carboxylic acid [2-[4-(3-chloro-4-fluoro-phenoxy)-phenyl]-1-(3-methyl-[1,2,4]oxadiazol-5-yl)-ethyl]-amide (0.07 g) was prepared from 2-[4-(3-Chloro-4-fluoro-phenoxy)-phenyl]-1-(3-methyl-[1,2,4]oxadiazol-5-yl)-ethylamine hydrochloride [0.07 g, 0.182 mmol, which was prepared from [2-[4-(3-Chloro-4-fluoro-phenoxy)-phenyl]-1-(3-methyl-[1,2,4]oxadiazol-5-yl)-ethyl]-carbamic acid tert-butyl ester by the hydrolysis of BOC group using the general procedure N] and 5-Chloro 4-methoxy-4′-trifluoromethyl-biphenyl-3-carboxylic acid (as in example 42) (0.053 g, 0.18 mmol) following general procedure A. 5-Chloro-4-hydroxy-4′-trifluoromethyl-biphenyl-3-carboxylic acid [2-[4-(3-chloro-4-fluoro-phenoxy)-phenyl]-1-(3-methyl-[1,2,4]oxadiazol-5-yl)-ethyl]-amide (20 mg) was obtained upon methyl ether hydrolysis using the general procedure P. 1HNMR (400 MHz, CDCl3): 2.40 (s, 3H), 3.39 (m, 2H), 5.79 (dd, 1H), 6.84 (m, 1H), 6.90 (d, 2H), 7.02 (1 H), 7.04-7.17 (m, 4H), 7.50 (d, 1H), 7.61 (d, 2H), 7.71 (d, 2H), 7.78 (d, 1H), 12.03 (s, 1H).

Sources & evidence

ORD record
ord-296bfae4d5e04268aa4236dd82842265
Source dataset
uspto-grants-2008_12
Patent number
US07459472B2

Reaction notes

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