Hydrochloric Acid → (1R,3S,4S,5R)-3-[4-Amino-3-fluoro-5-((R)-2,2,2-trifluoro-1-methoxymethyl-ethoxy)-benzyl]-5-{[1-(2,2-dimethyl-propyl)-1H-pyrazol-4-ylmethyl]-amino}-1-oxo-tetra-hydro-thiopyran-4-ol dihydrochloride

HRID 420328Notes

Reaction equation

HRID 420328 reaction equation
[ClH:1].[NH2:2][C@@H:3]1[C@@H:8]([OH:9])[C@H:7]([CH2:10][C:11]2[CH:16]=[C:15]([O:17][C@H:18]([CH2:23][O:24][CH3:25])[C:19]([F:22])([F:21])[F:20])[C:14]([N+:26]([O-])=O)=[C:13]([F:29])[CH:12]=2)[CH2:6][S@@:5](=[O:30])[CH2:4]1.[CH3:31][C:32]([CH3:42])([CH3:41])[CH2:33][N:34]1[CH:38]=[C:37]([CH:39]=O)[CH:36]=[N:35]1.Cl>CCOCC>[ClH:1].[ClH:1].[NH2:26][C:14]1[C:15]([O:17][C@H:18]([CH2:23][O:24][CH3:25])[C:19]([F:22])([F:21])[F:20])=[CH:16][C:11]([CH2:10][C@H:7]2[C@H:8]([OH:9])[C@@H:3]([NH:2][CH2:39][C:37]3[CH:36]=[N:35][N:34]([CH2:33][C:32]([CH3:42])([CH3:41])[CH3:31])[CH:38]=3)[CH2:4][S@:5](=[O:30])[CH2:6]2)=[CH:12][C:13]=1[F:29]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 66649645(1R,3R,4S,5S)-3-amino-5-[3-fluoro-4-nitro-5-((R)-2,2,2-trifluoro-1-methoxymethyl-ethoxy)-benzyl]-1-oxo-tetrahydro-thiopyran-4-ol hydrochlorideHCID 866395471-(2,2-Dimethyl-propyl)-1H-pyrazole-4-carbaldehyde

Product 1

HCID 86639548(1R,3S,4S,5R)-3-[4-Amino-3-fluoro-5-((R)-2,2,2-trifluoro-1-methoxymethyl-ethoxy)-benzyl]-5-{[1-(2,2-dimethyl-propyl)-1H-pyrazol-4-ylmethyl]-amino}-1-oxo-tetra-hydro-thiopyran-4-ol dihydrochloride

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

The title compound can be prepared in an analogous manner as described for example 41 steps c) and d) from (1R,3R,4S,5S)-3-amino-5-[3-fluoro-4-nitro-5-((R)-2,2,2-trifluoro-1-methoxymethyl-ethoxy)-benzyl]-1-oxo-tetrahydro-thiopyran-4-ol hydrochloride and 1-(2,2-dimethyl-propyl)-1H-pyrazole-4-carbaldehyde and subsequent transformation into the hydrochloride salt with 5N HCl in Et2O to afford the title compound as a beige foam: TLC (CH2Cl2-MeOH 9:1) Rf=0.35; HPLC RtG3=1.51 min; ESIMS [M+H]+=565; 1H NMR (400 MHz, DMSO-d6): δ 7.53 (s, 1H), 7.34 (s, 1H), 6.72 (s, 1H), 6.64 (d, 1H), 5.12-5.06 (m, 1H), 4.96 (d, 1H), 4.59 (s, 2H), 3.84 (s, 2H), 3.77-3.64 (m, 3H), 3.48 (d, 1H), 3.33 (s, 3H), 3.18-3.05 (m, 3H), 2.98 (dd, 1H), 2.71 (d, 1H), 2.46-2.26 (m, 5H), 0.88 (s, 9H).

Sources & evidence

ORD record
ord-e44511b0502c44869e1f9ac9e071677f
Source dataset
uspto-grants-2012_01
Patent number
US08093406B2

Reaction notes

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