Methylamine → HCID 15434749, compound

HRID 1600882Notes

Reaction equation

HRID 1600882 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]2[NH:8][CH:9]=[C:10]([CH2:11][CH2:12]I)[C:5]2=[CH:4][CH:3]=1.[NH2:14][C@H:15](C(O)=O)CC1C=C2C(C=CC=C2)=CC=1.CN>C(O)C>[Cl:1][C:2]1[N:7]=[C:6]2[NH:8][CH:9]=[C:10]([CH2:11][CH2:12][NH:14][CH3:15])[C:5]2=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6329MethylamineHCID 1859152-NaphthylalanineHCID 15434748HCID 15434748, compound

Product 1

HCID 15434749HCID 15434749, compoundYield 29.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1 g (3.26 mM) of 6-Chloro-3-(2-iodo-ethyl)-1H-pyrrolo[2,3-b]pyridine and 0.49 g (3.26 mM) Nal were mixed together in 100 mL of an ethanol solution saturated with methyl amine gas. This solution was heated to 100° C. in a steel bomb for 12 hours. The reaction mixture was cooled to room temperature and the solvent evaporated. The residue was chromatographed on silica using a mixture of 10:1 CH2Cl6 : CH3OH as the elutant. The appropriate fractions were combined and evaporated. The residue was crystallized from isopropyl ether-methanol to yield 140 mg of [2-(6-Chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-ethyl]-methyl-amine. MP=214-215° C. NMR (D6DMSO) δ11.75 (s, 1H), 8.08 (d, 1H), 7.41 (s, 1H), 7.15 (d, 1H), 3.20 (t, 2H), 3.02 (t, 2H), 2.60 (s, 3H). 13C NMR (D6DMSO) 147.5, 143.2, 129.9, 124.8, 118.2, 114.8, 108.7, 48.4, 32.6, 21.6. Mass spectrum: m/e=210, 212(P+1, P+3).

Workup

  1. customthe solvent evaporated
  2. customThe residue was chromatographed on silica using
  3. additiona mixture of 10:1 CH2Cl6
  4. customevaporated
  5. customThe residue was crystallized from isopropyl ether-methanol

Sources & evidence

ORD record
ord-e320469bf9014b1f800405e17af1ba56
Source dataset
uspto-grants-1999_11
Patent number
US05977131

Reaction notes

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