Benzenemethanamine, 3-chloro- → HCID 66957992, compound

HRID 570511Notes

Reaction equation

HRID 570511 reaction equation
C[Al](C)C.CO[C:7]([C:9]1[S:10][CH:11]=[CH:12][C:13]=1[NH:14][C:15]1[C:16]2[C:23]([CH3:24])=[CH:22][NH:21][C:17]=2[N:18]=[CH:19][N:20]=1)=[O:8].[Cl:25][C:26]1[CH:27]=[C:28]([CH:31]=[CH:32][CH:33]=1)[CH2:29][NH2:30]>C1(C)C=CC=CC=1.O>[Cl:25][C:26]1[CH:27]=[C:28]([CH:31]=[CH:32][CH:33]=1)[CH2:29][NH:30][C:7]([C:9]1[S:10][CH:11]=[CH:12][C:13]=1[NH:14][C:15]1[C:16]2[C:23]([CH3:24])=[CH:22][NH:21][C:17]=2[N:18]=[CH:19][N:20]=1)=[O:8]

Participants

6

Reactant 3

HCID 77802Benzenemethanamine, 3-chloro-HCID 16682925TrimethylaluminumHCID 66958015HCID 66958015, compound

Product 1

HCID 66957992HCID 66957992, compoundYield 50.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
70 °C

Procedure

Trimethyl aluminum (0.35 mL, 0.69 mmol, 2M in toluene) was added to a solution of 3-(5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)-thiophene-2-carboxylic acid methyl ester (50 mg, 0.17 mmol) and 3-chlorobenzylamine (0.11 mL, 0.87 mmol) in toluene (2 mL), and stirred overnight at 70° C. The reaction mixture was cooled to room temperature, diluted with H2O and EtOAC, and filtered through an Extrelut column. The column was washed with EtOAC and the filtrate was concentrated. The crude product was purified via Biotage eluting with a gradient of 0 to 100% EtOAC in hexanes to provide the desire product (34 mg, 49% yield) as an off-white solid. LC-MS (M+H=398, obsd.=398).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationfiltered through an Extrelut column
  3. washThe column was washed with EtOAC
  4. concentrationthe filtrate was concentrated
  5. customThe crude product was purified via Biotage
  6. washeluting with a gradient of 0 to 100% EtOAC in hexanes

Sources & evidence

ORD record
ord-63288e258ce14e2d98acc7bd86dc4513
Source dataset
uspto-grants-2015_05
Patent number
US09023847B2

Reaction notes

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