4-Methyl-1-piperazinecarbonyl chloride → HCID 58529677, compound

HRID 1972847Notes

Reaction equation

HRID 1972847 reaction equation
[CH2:1]([N:8]1[CH:16]=[C:15]2[C:10]([CH:11]=[C:12]([C:17]3[CH:18]=[C:19]([CH:27]4[CH2:31][CH2:30][NH:29][CH2:28]4)[N:20]4[C:25]=3[C:24]([NH2:26])=[N:23][CH:22]=[N:21]4)[CH:13]=[CH:14]2)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:32][N:33]1[CH2:38][CH2:37][N:36]([C:39](Cl)=[O:40])[CH2:35][CH2:34]1>C(Cl)Cl>[CH2:1]([N:8]1[CH:16]=[C:15]2[C:10]([CH:11]=[C:12]([C:17]3[CH:18]=[C:19]([CH:27]4[CH2:31][CH2:30][N:29]([C:39]([N:36]5[CH2:37][CH2:38][N:33]([CH3:32])[CH2:34][CH2:35]5)=[O:40])[CH2:28]4)[N:20]4[C:25]=3[C:24]([NH2:26])=[N:23][CH:22]=[N:21]4)[CH:13]=[CH:14]2)=[N:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 30169354-Methyl-1-piperazinecarbonyl chlorideHCID 58529326HCID 58529326, compound

Product 1

HCID 58529677HCID 58529677, compoundYield 20.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-(2-benzyl-2H-indazol-6-yl)-7-pyrrolidin-3-ylpyrrolo[2,1-f][1,2,4]triazin-4-amine (60 mg, 0.147 mmol) in CH2Cl2 (2 mL), the solution made in Step 1 of 4-methylpiperazine-1-carbonyl chloride (62 mg, 0.163 mmol) was added. The reaction mixture was stirred at rt overnight. The reaction was then partitioned between EtOAc (50 mL) and 10% aqueous potassium carbonate. (20 mL). The aqueous layer was extracted with EtOAc (20 mL). The combined organic layers were washed with brine, dried with sodium sulfate and concentrated under vacuum. The residue was triturated with ether to yield 16 mg (20%) of product. 1H NMR (300 MHz, DMSO-d6) δ 8.54 (s, 1 H), 7.91 (s, 1 H), 7.78 (d 1 H), 7.58 (s, 1 H), 7.33 (m, 5 H), 7.13 (d, 1 H), 6.66 (s, 1 H), 5.64 (s, 2 H), 3.90 (m, 1 H), 3.60-3.30 (m, 8 H), 2.50-2.00 (m, 9 H); ES-MS m/z 536.3 [M+H]+, HPLC RT (min) 2.13.

Workup

  1. additionwas added
  2. customThe reaction was then partitioned between EtOAc (50 mL) and 10% aqueous potassium carbonate
  3. extractionThe aqueous layer was extracted with EtOAc (20 mL)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried with sodium sulfate
  6. concentrationconcentrated under vacuum
  7. customThe residue was triturated with ether

Sources & evidence

ORD record
ord-3c48860aec2f40b6b7a62e1b98c81279
Source dataset
uspto-grants-2013_04
Patent number
US08431695B2

Reaction notes

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