Methanesulfonyl chloride → HCID 58964299, compound

HRID 1626182Notes

Reaction equation

HRID 1626182 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][O:10][C:11]2[CH:16]=[CH:15][C:14]([NH:17][C:18](=[O:29])[C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:28])([F:27])[F:26])[CH:20]=3)=[CH:13][C:12]=2[C:30]2[N:31]([CH3:36])[N:32]=[CH:33][C:34]=2[Cl:35])[CH2:4][CH2:3]1.[CH3:37][S:38](Cl)(=[O:40])=[O:39]>CC(N(C)C)=O>[Cl:35][C:34]1[CH:33]=[N:32][N:31]([CH3:36])[C:30]=1[C:12]1[CH:13]=[C:14]([NH:17][C:18](=[O:29])[C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:27])([F:28])[F:26])[CH:20]=2)[CH:15]=[CH:16][C:11]=1[O:10][CH2:9][CH2:8][N:5]1[CH2:4][CH2:3][CH:2]([NH:1][S:38]([CH3:37])(=[O:40])=[O:39])[CH2:7][CH2:6]1

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 58964273HCID 58964273, compound

Product 1

HCID 58964299HCID 58964299, compoundYield 35.6%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

N-[4-[2-(4-Amino-piperidin-1-yl)-ethoxy]-3-(4-chloro-2-methyl-2H-pyrazol-3-yl)-phenyl]-3-trifluoromethyl-benzamide (0.038 g, 0.073 mmol) was dissolved in DMA (2.0 mL) in a vial with stir bar. Methanesulfonyl chloride (0.0085 g, 0.11 mmol) was added and the reaction was stirred at rt overnight. The reaction was concentrated, added to NaHCO3 (5 mL), and the solution was extracted with EtOAc (2×20 mL). The organic extracts were dried (Na2SO4), filtered, concd and purified by prep HPLC to afford the title compound (0.016 g, 0.026 mmol, 35%, TFA salt) as a white solid. LCMS m/z (%)=600 (M+H35Cl, 100), 602 (M+H37Cl, 36). 1H NMR (400 MHz, DMSO-d6) δ: 10.54 (s, 1H), 9.30 (s, 1H), 8.30 (s, 1H), 8.26 (d, J=8.0 Hz, 1H), 7.97 (m, 2H), 7.80 (m, 1H), 7.72 (d, J=2.6 Hz, 1H), 7.68 (s, 1H), 7.31 (m, 1H), 4.40 (m, 1H), 4.32 (m, 1H), 3.69 (s, 3H), 3.50-2.90 (m, 7H), 2.95 (s, 3H), 2.00-1.50 (m, 4H).

Workup

  1. stirringthe reaction was stirred at rt overnight
  2. concentrationThe reaction was concentrated
  3. additionadded to NaHCO3 (5 mL)
  4. extractionthe solution was extracted with EtOAc (2×20 mL)
  5. dry with materialThe organic extracts were dried (Na2SO4)
  6. filtrationfiltered
  7. customconcd and purified by prep HPLC

Sources & evidence

ORD record
ord-83905ec2c6af46d89dad7ef2b9aae797
Source dataset
uspto-grants-2014_07
Patent number
US08785441B2

Reaction notes

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