(3R,4S)-pyrrolidine-3,4-diol → HCID 89906154, compound

HRID 924129Notes

Reaction equation

HRID 924129 reaction equation
[Br:1][C:2]1[C:3](Cl)=[N:4][CH:5]=[C:6]([CH:21]=1)[C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][C:17]([Cl:20])([F:19])[F:18])=[CH:12][CH:11]=1)=[O:8].[NH:23]1[CH2:27][C@H:26]([OH:28])[C@H:25]([OH:29])[CH2:24]1>>[Br:1][C:2]1[C:3]([N:23]2[CH2:27][C@H:26]([OH:28])[C@H:25]([OH:29])[CH2:24]2)=[N:4][CH:5]=[C:6]([CH:21]=1)[C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][C:17]([Cl:20])([F:19])[F:18])=[CH:12][CH:11]=1)=[O:8]

Participants

3

Reactant 2

HCID 13329882(3R,4S)-pyrrolidine-3,4-diolHCID 725460895-bromo-6-chloro-N-(4-(chlorodifluoromethoxy)phenyl)nicotinamide

Product 1

HCID 89906154HCID 89906154, compound

Procedure

The title compound was prepared in an analogous fashion to that described in Stage 71.1 using 5-bromo-6-chloro-N-(4-(chlorodifluoromethoxy)phenyl)nicotinamide (Stage 169.2) and cis-pyrrolidine-3,4-diol (Stage 249.2). After purification by flash chromatography on Silica gel, the oily residue was taken-up in a toluene/MeOH mixture then evaporated to dryness under reduced pressure and dried to yield the title product as a white amorphous solid. UPLC-MS (Condition 3) tR=1.0 min, m/z=477.8-479.9 [M+H], m/z=475.8-477.9 [M−H].

Workup

  1. customThe title compound was prepared in an analogous fashion to
  2. customAfter purification by flash chromatography on Silica gel
  3. customthen evaporated to dryness under reduced pressure
  4. customdried

Sources & evidence

ORD record
ord-6e8d711fd6784d4884cd629b46eb65ae
Source dataset
uspto-grants-2016_03
Patent number
US09278981B2

Reaction notes

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