Methylamine → HCID 178484094, compound

HRID 2271556Notes

Reaction equation

HRID 2271556 reaction equation
CS(O[CH2:6][C@H:7]1[CH2:12][CH2:11][C@H:10]([NH:13][C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[C:21]([Br:24])[CH:22]=3)[N:17]=[CH:16][C:15]=2[C:25]([CH:27]2[CH2:29][CH2:28]2)=[O:26])[CH2:9][CH2:8]1)(=O)=O.[CH3:30][NH2:31]>>[Br:24][C:21]1[CH:22]=[C:23]2[C:18](=[CH:19][CH:20]=1)[N:17]=[CH:16][C:15]([C:25]([CH:27]1[CH2:28][CH2:29]1)=[O:26])=[C:14]2[NH:13][C@H:10]1[CH2:11][CH2:12][C@H:7]([CH2:6][NH:31][CH3:30])[CH2:8][CH2:9]1

Participants

3

Reactant 2

HCID 6329MethylamineHCID 178505297HCID 178505297, compound

Product 1

HCID 178484094HCID 178484094, compoundYield 28%

Conditions

Temperature
120 °C

Procedure

A suspension of (trans-4-((6-bromo-3-(cyclopropanecarbonyl)quinolin-4-yl)amino)cyclohexyl)methyl methanesulfonate (175 mg, 0.36 mmol) in methylamine (2.0 M solution in THF, 4.0 mL, 8.0 mmol) in a sealed vessel was heated under microwave irradiation conditions to 120° C. for 2 h. The solution was cooled to room temperature and concentrated. The resultant residue was purified by preparative HPLC (C18 silica, 10-90% methanol/water with 0.05% TFA). The residue was eluted through an ion-exchange column (using methanol and 7 N methanol in ammonia) to obtain the desired product (42 mg, 28%) a white solid. ESI MS m/z 416 [C21H26BrN3O+H]+

Workup

  1. temperatureThe solution was cooled to room temperature
  2. concentrationconcentrated
  3. customThe resultant residue was purified by preparative HPLC (C18 silica, 10-90% methanol/water with 0.05% TFA)
  4. washThe residue was eluted through an ion-exchange column (using methanol and 7 N methanol in ammonia)

Sources & evidence

ORD record
ord-f4fce93d75c54ad5a36b321351c4a99d
Source dataset
uspto-grants-2015_09
Patent number
US09120749B2

Reaction notes

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