Methanesulfonamide → HCID 86703562, compound

HRID 1849691Notes

Reaction equation

HRID 1849691 reaction equation
[CH:1]1([C:4]2[C:5]([O:14][CH2:15][C:16]3([CH3:24])[CH2:23][CH2:22][C:19]4([CH2:21][CH2:20]4)[CH2:18][CH2:17]3)=[CH:6][C:7]([F:13])=[C:8]([CH:12]=2)[C:9](O)=[O:10])[CH2:3][CH2:2]1.Cl.C(N=C=NCCCN(C)C)C.[CH3:37][S:38]([NH2:41])(=[O:40])=[O:39]>ClCCl.CN(C)C1C=CN=CC=1>[CH:1]1([C:4]2[C:5]([O:14][CH2:15][C:16]3([CH3:24])[CH2:23][CH2:22][C:19]4([CH2:21][CH2:20]4)[CH2:18][CH2:17]3)=[CH:6][C:7]([F:13])=[C:8]([CH:12]=2)[C:9]([NH:41][S:38]([CH3:37])(=[O:40])=[O:39])=[O:10])[CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 72879MethanesulfonamideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86703561HCID 86703561, compound

Product 1

HCID 86703562HCID 86703562, compoundYield 55.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 5-cyclopropyl-2-fluoro-4-((6-methylspiro[2.5]octan-6-yl)methoxy)benzoic acid (0.085 g, 0.256 mmol) in dichloromethane (7 mL) was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.076 g, 0.384 mmol) and 4-dimethylaminopyridine (0.072 g, 0.589 mmol). The reaction mixture was stirred at ambient temperature for 10 minutes; methanesulfonamide (0.039 g, 0.41 mmol) was added and the stirring continued at ambient temperature for 17 hours. The reaction mixture was concentrated, diluted with ethyl acetate (20 mL) and washed with 5% aqueous hydrochloric acid solution (10 mL). The organic layer was separated and washed with water and brine, dried over anhydrous sodium sulfate and concentrated in vacuo. Purification of the residue by column chromatography (0% to 30% ethyl acetate in hexanes) afforded the title compound (0.058 g, 55%) as a white solid: 1H NMR (300 MHz, CDCl3) δ 8.70 (d, J=16.5 Hz, 1H), 7.59 (d, J=9.0 Hz, 1H), 6.58 (d, J=14.6 Hz, 1H), 3.74 (s, 2H), 3.40 (s, 3H), 2.09-1.95 (m, 1H), 1.69-1.42 (m, 6H), 1.29-1.02 (m, 5H), 0.96-0.87 (m, 2H), 0.67-0.60 (m, 2H), 0.31-0.16 (m, 4H); MS (ES−) m/z 408.3 (M−1).

Workup

  1. waitthe stirring continued at ambient temperature for 17 hours
  2. concentrationThe reaction mixture was concentrated
  3. additiondiluted with ethyl acetate (20 mL)
  4. washwashed with 5% aqueous hydrochloric acid solution (10 mL)
  5. customThe organic layer was separated
  6. washwashed with water and brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated in vacuo
  9. customPurification of the residue by column chromatography (0% to 30% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-87064ca3e0df4ddb8ab376040dc9b790
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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