Triethylamine → (S)-N-(3-bromophenyl)-2-methyl-4-(5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-N'-(methylsulfonyl)piperazine-1-carboximidamide

HRID 1892139Notes

Reaction equation

HRID 1892139 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH:8][C:9](=[N:17][S:18]([CH3:21])(=[O:20])=[O:19])OC2C=CC=CC=2)[CH:5]=[CH:6][CH:7]=1.[CH3:22][C:23]1[C:31]2[C:30]([N:32]3[CH2:37][CH2:36][NH:35][C@@H:34]([CH3:38])[CH2:33]3)=[N:29][CH:28]=[N:27][C:26]=2[NH:25][CH:24]=1.C(N(CC)CC)C>CC#N>[Br:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]([N:35]2[CH2:36][CH2:37][N:32]([C:30]3[C:31]4[C:23]([CH3:22])=[CH:24][NH:25][C:26]=4[N:27]=[CH:28][N:29]=3)[CH2:33][C@@H:34]2[CH3:38])=[N:17][S:18]([CH3:21])(=[O:19])=[O:20])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 68725987phenyl N-3-bromophenyl-N'-(methylsulfonyl)carbamimidateHCID 68958720(S)-5-methyl-4-(3-methylpiperazin-1-yl)-7H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 68957478(S)-N-(3-bromophenyl)-2-methyl-4-(5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-N'-(methylsulfonyl)piperazine-1-carboximidamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The carbamimidate from step B (100 mg, 0.27 mmol), (S)-5-methyl-4-(3-methylpiperazin-1-yl)-7H-pyrrolo[2,3-d]pyrimidine, from Example 1, step B (63 mg, 0.27 mmol), and triethylamine (77 μl, 0.27 mmol) were combined in MeCN (1.5 ml) and heated to reflux for 2 hours. The mixture was concentrated and purified by preparative HPLC to afford (S)—N-(3-bromophenyl)-2-methyl-4-(5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-N′-(methylsulfonyl)piperazine-1-carboximidamide.

Workup

  1. temperatureheated
  2. temperatureto reflux for 2 hours
  3. concentrationThe mixture was concentrated
  4. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-664ab8a1e0fa4135be5a8ddf6830ef78
Source dataset
uspto-grants-2013_08
Patent number
US08507672B2

Reaction notes

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