2-(Methylsulfonyl)ethanamine → HCID 57974158, compound

HRID 1362888Notes

Reaction equation

HRID 1362888 reaction equation
[F:1][C:2]1[C:3]([NH:17][C:18]2[CH:29]=[CH:28][CH:27]=[CH:26][C:19]=2[C:20]([NH:22][CH:23]([CH3:25])[CH3:24])=[O:21])=[N:4][C:5]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([CH:15]=O)=[CH:11][CH:10]=2)=[N:6][CH:7]=1.[CH3:30][S:31]([CH2:34][CH2:35][NH2:36])(=[O:33])=[O:32]>C(Cl)Cl>[F:1][C:2]1[C:3]([NH:17][C:18]2[CH:29]=[CH:28][CH:27]=[CH:26][C:19]=2[C:20]([NH:22][CH:23]([CH3:25])[CH3:24])=[O:21])=[N:4][C:5]([NH:8][C:9]2[CH:10]=[CH:11][C:12]([CH2:15][NH:36][CH2:35][CH2:34][S:31]([CH3:30])(=[O:33])=[O:32])=[CH:13][CH:14]=2)=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 43405612-(Methylsulfonyl)ethanamineHCID 57974221HCID 57974221, compound

Product 1

HCID 57974158HCID 57974158, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2-({5-Fluoro-2-[(4-formylphenyl)amino]-4-pyrimidinyl}amino)-N-(1-methylethyl)benzamide (80 mg, 0.2 mmol, 1.0 eq), [2-(methylsulfonyl)ethyl]amine (100 mg, 0.6 mmol, 3.0 eq), and CH2Cl2 (2.0 mL) were added to a vessel, which was sealed and stirred at room temperature for 16 h. Solvent was removed by evaporation to leave a residue. NaBCNH4 (37 mg, 0.6 mmol, 3.0 eq) in CH2Cl2 (2.0 mL) was added was added to the residue and the reaction mixture was stirred at room temperature until the reaction was substantially complete, as determined by HPLC. The final product was purified by preparative HPLC using water (0.1% formic acid); acetonitrile (0.1% formic acid) as mobile phase. The desired compound was isolated as an off-white solid. (20 mg, 20% yield) MS: M(C24H29FN6O3S)=500.60, (M+H)+=501.

Workup

  1. customwhich was sealed
  2. customSolvent was removed by evaporation
  3. customto leave a residue
  4. additionwas added to the residue
  5. stirringthe reaction mixture was stirred at room temperature until the reaction
  6. customThe final product was purified by preparative HPLC

Sources & evidence

ORD record
ord-8ed396cd039b4823a5307b312230175f
Source dataset
uspto-grants-2011_02
Patent number
US07884098B2

Reaction notes

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