Hydrochloric Acid → HCID 57386047, compound

HRID 420269Notes

Reaction equation

HRID 420269 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:30]=[CH:31][CH:32]=1)[CH2:8][NH:9][C@@H:10]1[C@@H:15]([OH:16])[C@H:14]([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[C:20]([F:27])[CH:19]=2)[CH2:13][S:12](=[O:29])(=[O:28])[CH2:11]1)([CH3:4])([CH3:3])[CH3:2].CCN(C(C)C)C(C)C.[C:42](C1NC=CN=1)(C1NC=CN=1)=[O:43].Cl>C(#N)C.CN(C1C=CN=CC=1)C>[C:1]([C:5]1[CH:6]=[C:7]([CH:30]=[CH:31][CH:32]=1)[CH2:8][N:9]1[C@@H:10]2[C@H:15]([C@H:14]([CH2:17][C:18]3[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[C:20]([F:27])[CH:19]=3)[CH2:13][S:12](=[O:28])(=[O:29])[CH2:11]2)[O:16][C:42]1=[O:43])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 57386562HCID 57386562, compound

Product 1

HCID 57386047HCID 57386047, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6342AcetonitrileSolvent

Procedure

To a suspension of (3R*,4S*,5S*)-3-(3-tert-butyl-benzylamino)-5-(3-fluoro-4-nitro-benzyl)-1,1-dioxo-hexahydro-1lambda*6*-thiopyran-4-ol (4.4 g, 8.7 mmol) in ACN was added at 25° C. the DIPEA and the carbonyl-diimidazole. After addition of a catalytic amount of DMAP, the clear reaction mixture was kept at 25° C. for 16 h. The reaction mixture was poured onto ice-water and acidified with 4N aq. HCl. The precipitate was filtered off and washed with H2O and Et2O, dried under reduced pressure for 6 h at 50° C. to yield the title product as light yellow crystals: TLC (toluene-THF 1:1) Rf=0.66; HPLC RtA=2.25 min; ESIMS [M+NH4]+=508; 1H NMR (400 MHz, DMSO-d6): δ 8.11 (dd, 1H), 7.48 (dd, 1H), 7.38 (s, 1H), 7.28 (m, 3H), 7.12 (d, 1H), 4.41 (d, 1H), 4.20 (m, 2H), 3.72 (m, 2H), 3.42 (dd, 1H), 3.14 (d, 2H), 3.04 (dd, 1H), 2.76 (dd, 1H), 2.64 (m, 1H), 1.25 (s, 9H).

Workup

  1. additionThe reaction mixture was poured onto ice-water
  2. filtrationThe precipitate was filtered off
  3. washwashed with H2O and Et2O
  4. customdried under reduced pressure for 6 h at 50° C.

Sources & evidence

ORD record
ord-55061cf720f24ae4b7725dd309c5fe44
Source dataset
uspto-grants-2012_01
Patent number
US08093406B2

Reaction notes

Loading…