Phenyl chloroformate → HCID 58267948, compound

HRID 1918106Notes

Reaction equation

HRID 1918106 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:8]2[C:12]([NH2:13])=[CH:11][C:10]([CH:14]([CH3:16])[CH3:15])=[N:9]2)[CH:5]=[N:6][CH:7]=1.Cl[C:18]([O:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:19]>>[F:1][C:2]1[CH:3]=[C:4]([N:8]2[C:12]([NH:13][C:18](=[O:19])[O:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[CH:11][C:10]([CH:14]([CH3:16])[CH3:15])=[N:9]2)[CH:5]=[N:6][CH:7]=1

Participants

3

Reactant 2

HCID 15891Phenyl chloroformateHCID 66877614HCID 66877614, compound

Product 1

HCID 58267948HCID 58267948, compoundYield 35%

Procedure

Following the procedure for Example 282A Step 2, 1-(5-fluoropyridin-3-yl)-3-isopropyl-1H-pyrazol-5-amine was treated with phenyl chloroformate. Purification using silica gel chromatography eluting with MeOH/DCM (0-10%) afforded phenyl 1-(5-fluoropyridin-3-yl)-3-isopropyl-1H-pyrazol-5-ylcarbamate (235 mg, 35% yield) for steps B and C. 1H NMR (300 MHz, DMSO d6) δ 1.25 (s, 6H), 2.93 (m, 1H), 6.40 (s, 1H), 7.15 (bs, 2H), 7.29 (m, 2H), 7.42 (m, 3H), 8.00 (m, 1H), 8.65 (s, 1H), 8.72 (s, 1H), 10.32 (s, 1H); LC-MS (ESI) m/z 341 (M+H)+

Workup

  1. customPurification
  2. washeluting with MeOH/DCM (0-10%)

Sources & evidence

ORD record
ord-5a9f5759b0c54c959b7fda59c230c0c6
Source dataset
uspto-grants-2013_12
Patent number
US08618289B2

Reaction notes

Loading…