Hydrochloric Acid → (5RS)-3-(3-Fluoro-4-(1,2,5,6-tetrahydropyrid-4-yl)phenyl)-5-isoxazol-3-ylaminomethyl-4,5-dihydroisoxazole hydrochloride

HRID 1793680Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([C:21]2[CH2:25][CH:24]([CH2:26][N:27]([C:35]3[CH:39]=[CH:38][O:37][N:36]=3)C(OC(C)(C)C)=O)[O:23][N:22]=2)[CH:5]=[CH:6][C:7]=1[C:8]1[CH2:13][CH2:12][N:11](C(OC(C)(C)C)=O)[CH2:10][CH:9]=1.[ClH:40]>>[ClH:40].[F:1][C:2]1[CH:3]=[C:4]([C:21]2[CH2:25][CH:24]([CH2:26][NH:27][C:35]3[CH:39]=[CH:38][O:37][N:36]=3)[O:23][N:22]=2)[CH:5]=[CH:6][C:7]=1[C:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH:9]=1

Participants

Reactant 2

HCID 313Hydrochloric Acid

HCID 22022972(5RS)-3-(3-Fluoro-4-(1-t-butoxycarbonyl-1,2,5,6-tetrahydropyrid-4-yl)phenyl)-5-(N-(t-butoxycarbonyl)isoxazol-3-ylaminomethyl)-4,5-dihydroisoxazole

Product 1

HCID 17948112(5RS)-3-(3-Fluoro-4-(1,2,5,6-tetrahydropyrid-4-yl)phenyl)-5-isoxazol-3-ylaminomethyl-4,5-dihydroisoxazole hydrochloride

Procedure

(5RS)-3-(3-Fluoro-4-(1-t-butoxycarbonyl-1,2,5,6-tetrahydropyrid-4-yl)phenyl)-5-(N-(t-butoxycarbonyl)isoxazol-3-ylaminomethyl)-4,5-dihydroisoxazole (817 mg, 1.51 mM) was treated with ethanolic hydrogen chloride under essentially the conditions of the equivalent intermediate of Example 1, to give the desired product directly from the reaction mixture after washing with diethyl ether (310 mg). MS(ESP): 343 (MH+) for C18H19FN4O2 NMR (DMSO-d6) δ: 2.65 (br, 2H); 3.19 (dd partly overlapped, 1H); 3.23 (overlapping m, 4H); 3.47 (dd, 1H); 3.71 (br, 2H); 4.91 (m, 1H); 5.97 (d, 1H); 6.09 (br, 1H); 7.46 (overlapping m, 3H); 8.34 (d, 1H); 9.51 (br, 2H).

Sources & evidence

ORD record: ord-a96cc9bd82a54b5d901a11899a87c7f3
Source dataset: uspto-grants-2006_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07081538B1

Reaction notes

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