Methylamine → HCID 25172458, compound

HRID 1095413Notes

Reaction equation

HRID 1095413 reaction equation
[C:1]1([S:7]([C:10]([C:13]2[CH:18]=[C:17]([N:19]3[CH2:24][CH2:23][O:22][CH2:21][C@@H:20]3[CH3:25])[N:16]=[C:15]([C:26]3[CH:32]=[CH:31][C:29]([NH2:30])=[CH:28][CH:27]=3)[N:14]=2)([CH3:12])[CH3:11])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N:33]1([C:38](N2C=CN=C2)=[S:39])C=CN=[CH:34]1.CN>C1COCC1.C(Cl)Cl>[C:1]1([S:7]([C:10]([C:13]2[CH:18]=[C:17]([N:19]3[CH2:24][CH2:23][O:22][CH2:21][C@@H:20]3[CH3:25])[N:16]=[C:15]([C:26]3[CH:27]=[CH:28][C:29]([NH:30][C:38]([NH:33][CH3:34])=[S:39])=[CH:31][CH:32]=3)[N:14]=2)([CH3:12])[CH3:11])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 6329MethylamineHCID 802641,1'-ThiocarbonyldiimidazoleHCID 59508406HCID 59508406, compound

Product 1

HCID 25172458HCID 25172458, compoundYield 59.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

A solution of 4-[4-[2-(benzenesulfonyl)propan-2-yl]-6-[(3S)-3-methylmorpholin-4-yl]pyrimidin-2-yl]aniline (0.091 g, 0.2 mmol) in THF (1.0 mL) was added to a solution of di(imidazol-1-yl)methanethione (0.050 g, 0.28 mmol) in DCM (1.0 mL) and the resulting solution was stirred at 40° C. for 30 minutes. A solution of methylamine (2.0M in THF, 0.5 mL, 1.0 mmol) was added and the reaction was stirred at 40° C. for 30 minutes and the solvent was evaporated. The crude material was purified by preparative HPLC to give the desired material as a solid (63 mg).

Workup

  1. stirringthe reaction was stirred at 40° C. for 30 minutes
  2. customthe solvent was evaporated
  3. customThe crude material was purified by preparative HPLC

Sources & evidence

ORD record
ord-d96ef49e8a7d46059f0046131983f714
Source dataset
uspto-grants-2012_03
Patent number
US08138183B2

Reaction notes

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