Triethylamine → (S)-N-(3-bromo-4-fluorophenyl)-2-methyl-4-(5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperazine-1-carboxamide

HRID 1892119Notes

Reaction equation

HRID 1892119 reaction equation
ClC(Cl)(O[C:5](=[O:11])OC(Cl)(Cl)Cl)Cl.[Br:13][C:14]1[CH:15]=[C:16]([CH:18]=[CH:19][C:20]=1[F:21])[NH2:17].C(N(CC)CC)C.[CH3:29][C:30]1[C:38]2[C:37]([N:39]3[CH2:44][CH2:43][NH:42][C@@H:41]([CH3:45])[CH2:40]3)=[N:36][CH:35]=[N:34][C:33]=2[NH:32][CH:31]=1>C(Cl)Cl>[Br:13][C:14]1[CH:15]=[C:16]([NH:17][C:5]([N:42]2[CH2:43][CH2:44][N:39]([C:37]3[C:38]4[C:30]([CH3:29])=[CH:31][NH:32][C:33]=4[N:34]=[CH:35][N:36]=3)[CH2:40][C@@H:41]2[CH3:45])=[O:11])[CH:18]=[CH:19][C:20]=1[F:21]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 27792863-Bromo-4-fluoroanilineHCID 68958720(S)-5-methyl-4-(3-methylpiperazin-1-yl)-7H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 44543079(S)-N-(3-bromo-4-fluorophenyl)-2-methyl-4-(5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperazine-1-carboxamideYield 14.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a solution of triphosgene (0.30 g, 1 mmol) in CH2Cl2 (70 ml) at −5° C. were added 3-bromo-4-fluoroaniline (0.19 g, 1 mmol) in CH2Cl2 (20 ml) and triethylamine (0.60 ml, 4.3 mmol). The reaction was stirred at room temperature for 20 min, then (S)-5-methyl-4-(3-methylpiperazin-1-yl)-7H-pyrrolo[2,3-d]pyrimidine from step B (0.23 g, 1 mmol) in CH2Cl2 (30 ml) was added. The mixture was stirred for 1.5 hours, then concentrated under vacuum. The residue was purified by prep HPLC to afford (S)—N-(3-bromo-4-fluorophenyl)-2-methyl-4-(5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperazine-1-carboxamide (65 mg) as a white solid.

Workup

  1. stirringThe mixture was stirred for 1.5 hours
  2. concentrationconcentrated under vacuum
  3. customThe residue was purified by prep HPLC

Sources & evidence

ORD record
ord-5d390de8ccc546e8a274e685328a3676
Source dataset
uspto-grants-2013_08
Patent number
US08507672B2

Reaction notes

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