Methyl Isocyanate → HCID 18545964, compound

HRID 1267164Notes

Reaction equation

HRID 1267164 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11]3[CH2:12][CH2:13][N:14]([CH2:17][CH2:18][CH:19]4[C:27]5[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=5)[NH:21][CH2:20]4)[CH2:15][CH:16]=3)=[CH:7][NH:8]2)=[CH:4][CH:3]=1.[C:28]([O-:33])(=[O:32])[C:29]([O-:31])=[O:30].[CH3:34][N:35]=[C:36]=[O:37]>ClCCl>[C:28]([OH:33])(=[O:32])[C:29]([OH:31])=[O:30].[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11]3[CH2:12][CH2:13][N:14]([CH2:17][CH2:18][CH:19]4[C:27]5[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=5)[N:21]([C:36]([NH:35][CH3:34])=[O:37])[CH2:20]4)[CH2:15][CH:16]=3)=[CH:7][NH:8]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 12228Methyl IsocyanateHCID 71081OxalateHCID 18545826HCID 18545826, compound

Product 1

HCID 18545964HCID 18545964, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 6-chloro-3-[1-[2-(2,3-dihydro-1H-indol-3-yl)ethyl]-1,2,3,6-tetrahydropyridin-4-yl]-1H-indole, oxalate 30a, as the free base, (3.6 g) in dichloromethane (100 ml) was added methylisocyanate (1.4 g) in dichloromethane (20 ml). The mixture was stirred at room temperature for 16 h, and the solvent was removed in vacuo. The residue was purified on silica gel eluted with ethyl acetate-ethanol-triethylamine (90:10:5) to give the crude product, which was recrystallized (methanol-ethyl acetate-ether) to give the title compound (1.8 g). 1H NMR (DMSO-d6) δ 1.60-1.70 (m, 1H), 1.95-2.05 (m, 1H), 2.40-2.60 (m, 4H), 2.60-2.75 (m, 5H), 3.15 (q, 2H), 3.35-3.50 (m, 1H), 3.55-3.65 (m, 1H), 4.00 (t, 1H), 6.10 (broad s, 1H), 6.55 (d, 1H), 6.85 (t, 1H), 7.05 (d, 1H), 7.10 (t, 1H), 7.20 (d, 1H), 7.45 (s, 2H), 7.80 (d, 1H), 7.85 (d, 1H), 11.25 (broad s, 1H). MS m/z (%): 437, 435 (MH+, 2%, 6%), 201 (54%), 189 (100%), 144 (64%).

Workup

  1. customthe solvent was removed in vacuo
  2. customThe residue was purified on silica gel
  3. washeluted with ethyl acetate-ethanol-triethylamine (90:10:5)
  4. customto give the crude product, which
  5. customwas recrystallized (methanol-ethyl acetate-ether)

Sources & evidence

ORD record
ord-ecb68c9d02b34516b0ea0a5bee06b35e
Source dataset
uspto-grants-2003_04
Patent number
US06552044B2

Reaction notes

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