HCID 89907938, compound → HCID 89908240, compound

HRID 525778Notes

Reaction equation

HRID 525778 reaction equation
[Cl:1][C:2]([F:32])([F:31])[O:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:30])[C:12]2[CH:17]=[C:16]([C:18]3[NH:22][N:21]=[CH:20][CH:19]=3)[C:15]([NH:23][CH2:24][CH:25]([OH:29])[CH2:26][CH2:27][OH:28])=[N:14][CH:13]=2)=[CH:6][CH:5]=1>CCCCCCC.CCO.CO>[Cl:1][C:2]([F:31])([F:32])[O:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:30])[C:12]2[CH:17]=[C:16]([C:18]3[NH:22][N:21]=[CH:20][CH:19]=3)[C:15]([NH:23][CH2:24][C@@H:25]([OH:29])[CH2:26][CH2:27][OH:28])=[N:14][CH:13]=2)=[CH:6][CH:5]=1

Participants

3

Reactant 1

HCID 89907938HCID 89907938, compound

Product 1

HCID 89908240HCID 89908240, compound

Reagents, catalysts & solvents 1

HCID 22386818heptane EtOH MeOHSolvent

Procedure

The title compound was prepared by chiral separation (Preparative chiral HPLC, ChiralPak® AS, 20 μm 50×500 mm, mobile phase: n-heptane/EtOH/MeOH (85:10:5)+0.05% DEA, flow rate 68 mL/min, wavelength: 210 nm) of a racemic mixture of N-(4-(chlorodifluoromethoxy)phenyl)-6-((2,4-dihydroxybutyl)amino)-5-(1H-pyrazol-5-yl)nicotinamide (Example 97), slower eluting isomer (Peak 2, tR=12.52 min). Or alternatively, in an analogous fashion to that described in Example 97 using (S)-benzyl(2,4-dihydroxybutyl)carbamate (Stage 98.1) as chiral starting material. HPLC chiral (Chiralpak® AS-H, eluent: n-heptane/EtOH/MeOH (80:12:8)+0.05% DEA, flow rate:1 mL/min, temperature: RT, DAD 300 nm.): tR=9.31 min.

Workup

  1. washslower eluting isomer (Peak 2, tR=12.52 min)
  2. customHPLC chiral (Chiralpak® AS-H, eluent: n-heptane/EtOH/MeOH (80:12:8)+0.05% DEA, flow rate:1 mL/min, temperature: RT, DAD 300 nm.)

Sources & evidence

ORD record
ord-9020ba3d6902420d9f00bb9a04b64048
Source dataset
uspto-grants-2016_05
Patent number
US09340537B2

Reaction notes

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