4-Methylmorpholine → HCID 58529272, compound

HRID 1972815Notes

Reaction equation

HRID 1972815 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[O:32][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.[CH3:33][N:34]1[CH2:39][CH2:38][N:37]([C:40](Cl)=[O:41])[CH2:36][CH2:35]1.CN1CCOCC1>ClCCl.CO.CCOC(C)=O.C(=O)([O-])[O-].[Na+].[Na+]>[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[O:32][CH2:31][CH2:30][N:29]([C:40]([N:37]5[CH2:38][CH2:39][N:34]([CH3:33])[CH2:35][CH2:36]5)=[O:41])[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

Participants

8

Reactant 3

HCID 79724-MethylmorpholineHCID 30169354-Methyl-1-piperazinecarbonyl chlorideHCID 58529811HCID 58529811, compound

Product 1

HCID 58529272HCID 58529272, compoundYield 67.6%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolventHCID 10340Sodium CarbonateSolvent

Procedure

A solution of 5-(2-benzyl-2H-indazol-6-yl)-7-morpholin-2-ylpyrrolo[2,1-f][1,2,4]triazin-4-amine (59.1 mg, 0.11 mmol) in dichloromethane (1 mL) was cooled to 0° C. and treated with 4-methylpiperazine-1-carbonyl chloride (18 mg, 0.11 mmol) and N-methylmorpholine (28 mg, 0.28 mmol). After stirring for 1 h at rt, the reaction was diluted with 1 mL MeOH and diluted with EtOAc and 1N sodium carbonate solution. The organic layer was dried with sodium sulfate and concentrated in vacuo. The residue was triturated with acetonitrile to provide 41 mg (67%) of the desired product as an off-white solid. 1H NMR (300 MHz, DMSO-d6) δ 8.55 (s, 1 H), 7.95 (d, 1 H, J=3 Hz), 7.81 (d, 1 H, J=9 Hz), 7.61 (s, 1 H), 7.27-7.40 (m, 5H), 7.14 (d, 1H, J=9 Hz), 6.81 (d, 1 H, J=4 Hz), 5.65 (s, 2 H), 5.10-5.15 (m, 1H), 4.45-4.55 (m, 1 H), 3.95-4.25 (m, 3H), 3.65-3.85 (m, 3H), 3.49-3.60 (m, 1H), 3.30 (s, 3H), 3.35-3.25 (m, 1H), 3.14-3.25 (m, 1H); ES-MS Ink 552.1 [M+H]+, HPLC RT (min) 2.21.

Workup

  1. dry with materialThe organic layer was dried with sodium sulfate
  2. concentrationconcentrated in vacuo
  3. customThe residue was triturated with acetonitrile

Sources & evidence

ORD record
ord-99ea3c53dc4f4476bb93ebbf7509582f
Source dataset
uspto-grants-2013_04
Patent number
US08431695B2

Reaction notes

Loading…