Triethylamine → HCID 86695474, compound

HRID 1520524Notes

Reaction equation

HRID 1520524 reaction equation
Cl.Cl.[Br:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2([NH2:13])[CH2:12][CH2:11]2)=[N:8][CH:9]=1.C(N(CC)CC)C.[CH3:21][S:22](Cl)(=[O:24])=[O:23]>C(Cl)Cl>[Br:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2([NH:13][S:22]([CH3:21])(=[O:24])=[O:23])[CH2:11][CH2:12]2)=[N:8][CH:9]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 717421701-(5-Bromopyridin-2-yl)cyclopropanamine dihydrochloride

Product 1

HCID 86695474HCID 86695474, compoundYield 61.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Commercially available 1-(5-bromopyridin-2-yl)cyclopropanamine dihydrochloric acid salt (494 mg, 1.73 mmol) is dissolved in CH2Cl2 (11.5 mL, 0.15M) and had 3.1 eq. of triethylamine (543 mg, 5.36 mmol) added to it. 1.1 eq. of methanesulfonyl chloride (218 mg, 1.9 mmol) is then added and the mixture stirred for 16 hours. Dichloromethane (20 mL) is added and washed with NaHCO3 (sat, aq). The solvent is evaporated to give the title compound (310 mg): m/z (Cl) 293 [M+H].

Workup

  1. additionadded to it
  2. washwashed with NaHCO3 (sat, aq)
  3. customThe solvent is evaporated

Sources & evidence

ORD record
ord-c904a191ed504546bf07709161c43428
Source dataset
uspto-grants-2015_07
Patent number
US09073894B2

Reaction notes

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