Dimethylformamide → HCID 86724155, compound

HRID 1748833Notes

Reaction equation

HRID 1748833 reaction equation
C([CH2:4][CH2:5][CH:6]([C:20]1[CH:28]=[CH:27][C:23]([C:24]([OH:26])=O)=[CH:22][C:21]=1[CH3:29])[C:7]1[C:8]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=2)=[N:9][N:10]([CH3:13])[C:11]=1[Cl:12])(O)=O.[C:30]([O-:33])([O-:32])=O.[K+].[K+].I[CH3:37].CN([CH:41]=[O:42])C>>[Cl:12][C:11]1[N:10]([CH3:13])[N:9]=[C:8]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=2)[C:7]=1[CH:6]([C:20]1[CH:28]=[CH:27][C:23]([C:24]([O:42][CH3:41])=[O:26])=[CH:22][C:21]=1[CH3:29])[CH2:5][CH2:4][C:30]([O:33][CH3:37])=[O:32]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 86724153HCID 86724153, compound

Product 1

HCID 86724155HCID 86724155, compoundYield 89%

Procedure

To a mixture of 4-(3-carboxy-1-(5-chloro-1-methyl-3-(pyridin-2-yl)-1H-pyrazol-4-yl)propyl)-3-methylbenzoic acid (1.08 g, 2.61 mmol) and K2CO3 (1.44 g, 10.44 mmol) in DMF (20 mL) was added iodomethane (0.82 mL, 13.05 mmol). The mixture was stirred at rt for about 4 h then partitioned between EtOAc (150 mL) and H2O (150 mL). The organic layer was washed with brine (2×200 mL), dried over Na2SO4, filtered and concentrated in vacuo to give methyl 4-(1-(5-chloro-1-methyl-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-4-methoxy-4-oxobutyl)-3-methylbenzoate (1.03 g, 89%): LC-MS (Table 1, Method g) Rt=2.50 min, m/z 442 (M+H)+; 1H-NMR (DMSO, Bruker 400 MHz) δ 8.59-8.56 (m, 1H), 7.87-7.80 (m, 2H), 7.75-7.71 (m, 1H), 7.66 (d, J=1.4 Hz, 1H), 7.55 (d, J=8.2 Hz, 1H), 7.37-7.29 (m, 1H), 5.42-5.37 (m, 1H), 3.83 (s, 3H), 3.80 (s, 3H), 3.50 (s, 3H), 2.48-2.22 (m, 4H), 2.12 (s, 3H).

Workup

  1. customthen partitioned between EtOAc (150 mL) and H2O (150 mL)
  2. washThe organic layer was washed with brine (2×200 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3ffd022f247a40f39afc122c8c336fd6
Source dataset
uspto-grants-2015_10
Patent number
US09150592B2

Reaction notes

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