Triethylamine → HCID 44467332, compound

HRID 2046993Notes

Reaction equation

HRID 2046993 reaction equation
CCN(CC)CC.[CH:8]([O:11][C:12]1[CH:17]=[C:16]([CH:18]2[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]2)[C:15]([CH3:24])=[CH:14][C:13]=1[NH:25][C:26]1[N:27]=[C:28]([NH:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=2[S:43]([CH:46]([CH3:48])[CH3:47])(=[O:45])=[O:44])[C:29]2[C:34]([CH3:35])=[CH:33][NH:32][C:30]=2[N:31]=1)([CH3:10])[CH3:9].Br[CH2:50][C:51]([NH2:53])=[O:52]>CN(C=O)C>[CH:8]([O:11][C:12]1[C:13]([NH:25][C:26]2[N:27]=[C:28]([NH:36][C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=3[S:43]([CH:46]([CH3:48])[CH3:47])(=[O:44])=[O:45])[C:29]3[C:34]([CH3:35])=[CH:33][NH:32][C:30]=3[N:31]=2)=[CH:14][C:15]([CH3:24])=[C:16]([CH:18]2[CH2:23][CH2:22][N:21]([CH2:50][C:51]([NH2:53])=[O:52])[CH2:20][CH2:19]2)[CH:17]=1)([CH3:10])[CH3:9]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 696322-BromoacetamideHCID 44467331HCID 44467331, compound

Product 1

HCID 44467332HCID 44467332, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

82 uL of Et3N (0.69 mmol) was added into a solution of 40 mg N2-(2-isopropoxy-5-methyl-4-(piperidin-4-yl)phenyl)-N4-(2-(isopropylsulfonyl)phenyl)-5-methyl-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamine (11) (0.069 mmol) and 28.5 mg 2-bromoacetamide (0.207 mmol) in 1 mL of DMF. The reaction mixture was heated to 100° C. and stirred for 10 minutes under microwave irradiation. After cooling to room temperature, the solvent was removed under vacuum and the residue was redissolved in 1 mL of DMSO and purified by mass-triggered HPLC to give the title compound.

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe solvent was removed under vacuum
  3. dissolutionthe residue was redissolved in 1 mL of DMSO
  4. custompurified by mass-triggered HPLC

Sources & evidence

ORD record
ord-73e84d940b8c4d74b6e460481a3a400c
Source dataset
uspto-grants-2013_11
Patent number
US08592432B2

Reaction notes

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