Methylamine → HCID 58900137, compound

HRID 2242867Notes

Reaction equation

HRID 2242867 reaction equation
Cl.ClC1[N:4]([C:12]2[CH:30]=[CH:29][C:15]([O:16][CH2:17][CH2:18][CH2:19][N:20]3[CH2:25][CH2:24][CH:23]([C:26]([OH:28])=O)[CH2:22][CH2:21]3)=[CH:14][CH:13]=2)[N:5]=[C:6]2[C:11]=1[CH:10]=[CH:9][CH:8]=C2.[C:31]([Cl:36])(=O)[C:32](Cl)=O.[CH3:37][NH2:38]>C(Cl)Cl>[CH3:37][NH:38][C:26]([CH:23]1[CH2:22][CH2:21][N:20]([CH2:19][CH2:18][CH2:17][O:16][C:15]2[CH:14]=[CH:13][C:12]([N:4]3[C:31]([Cl:36])=[C:32]4[C:6]([CH:11]=[CH:10][CH:9]=[CH:8]4)=[N:5]3)=[CH:30][CH:29]=2)[CH2:25][CH2:24]1)=[O:28]

Participants

5

Reactant 3

HCID 6329MethylamineHCID 65578Oxalyl chlorideHCID 68704169HCID 68704169, compound

Product 1

HCID 58900137HCID 58900137, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-{3-[4-(3-chloro-indazol-2-yl)-phenoxy]-propyl}-piperidine-4-carboxylic acid hydrochloride (0.11 g, 0.25 mmol) in methylene chloride (11 mL) was added oxalyl chloride (0.12 g, 0.98 mmol) at room temperature, and stirred at room temperature for 3h. After the solvent was removed, the acid chloride was dissolved in THF and methylamine (40% in H2O, 3.8 g, 49 mmol) was added in one portion. The resulting reaction was stirred at room temperature for 3 h, and the THF was removed. The product was collected on a filter and air-dry for 8 h to provide the title compound (0.1 g, 99%). 1H NMR (400 MHz, CDCl3) δ 7.71(d, J=10.8 Hz, 1H), 7.62-7.56 (m, 3H), 7.37-7.33 (m, 1H), 7.17-7.14 (m, 2H), 7.04 (d, J=12 Hz, 2H), 5.48 (br, 1H), 4.10 (t, J=6 Hz, 2H), 3.00 (br d, J=12 Hz, 1H), 2.82 (d, J=4.8 Hz, 3H), 2.52 (t, J=6 Hz, 2H), 2.10-1.73 (m, 9H), LC/MS (APCI) m/z: 99%.

Workup

  1. customAfter the solvent was removed
  2. dissolutionthe acid chloride was dissolved in THF
  3. customThe resulting reaction
  4. stirringwas stirred at room temperature for 3 h
  5. customthe THF was removed
  6. customThe product was collected on
  7. filtrationa filter
  8. customair-dry for 8 h

Sources & evidence

ORD record
ord-ae7400aefac34b4eae09f5e295c66b2b
Source dataset
uspto-grants-2010_03
Patent number
US07674802B2

Reaction notes

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