Methyl Isocyanate → HCID 66760531, compound

HRID 889192Notes

Reaction equation

HRID 889192 reaction equation
[Cl:1][C:2]1[C:7]([CH2:8][O:9][C:10]2[C:18]3[N:17]=[C:16]([O:19][CH3:20])[N:15]([CH2:21][C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=4)[C:14]=3[CH:13]=[CH:12][CH:11]=2)=[C:6]([Cl:28])[CH:5]=[CH:4][C:3]=1[N:29]([CH3:46])[C:30](=[O:45])[CH2:31][NH:32][C:33]([CH:35]1[CH2:39][CH2:38][N:37]([CH:40]2[CH2:44][CH2:43][NH:42][CH2:41]2)[CH2:36]1)=[O:34].[CH3:47][N:48]=[C:49]=[O:50]>ClCCl>[Cl:1][C:2]1[C:7]([CH2:8][O:9][C:10]2[C:18]3[N:17]=[C:16]([O:19][CH3:20])[N:15]([CH2:21][C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=4)[C:14]=3[CH:13]=[CH:12][CH:11]=2)=[C:6]([Cl:28])[CH:5]=[CH:4][C:3]=1[N:29]([CH3:46])[C:30](=[O:45])[CH2:31][NH:32][C:33]([CH:35]1[CH2:39][CH2:38][N:37]([CH:40]2[CH2:44][CH2:43][N:42]([C:49]([NH:48][CH3:47])=[O:50])[CH2:41]2)[CH2:36]1)=[O:34]

Participants

4

Reactant 2

HCID 12228Methyl IsocyanateHCID 66760128HCID 66760128, compound

Product 1

HCID 66760531HCID 66760531, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of N-(2-((2,4-dichloro-3-(((2-methoxy-1-(pyridin-2-ylmethyl)-1H-benzo[d]imidazol-4-yl)oxy)methyl)phenyl)(methyl)amino)-2-oxoethyl)-[1,3′-bipyrrolidine]-3-carboxamide (0.20 g, 0.3 mmol) in dichloromethane (15 ml) was treated with methyl isocyanate (0.023 mL, 0.39 mmol) with stirring at room temperature for ten minutes. The reaction was evaporated, treated with methanol and evaporated to a tan solid, 0.20 g. This residue was purified by chromatography (silica gel, dichloromethane and methanol gradient) to afford 24 as a white solid, 0.06 g (28%), that was pure by LC/MS (+ESI) m/z 723 (M+), and was pure by 1HNMR (400 MHz, CDCl3) δ 8.58 (s, 1H), 7.59 (m, 1H), 7.49 (m, 2H), 7.29 (m, 1H), 7.19 (m, 1H), 7.05 (m, 1H), 6.80 (m, 2H), 5.69 (s, 2H), 5.29 (s, 2H), 4.20 (m, 4H), 3.80 (m, 1H), 3.50 (m, 3H), 3.25 (m, 5H), 2.85 (m, 7H), 2.55 (m, 2H), 2.10 (m, 5H). 13CNMR (100 MHz, CDCl3) δ 150, 148, 131, 130, 121, 122, 123, 108, 103, 65, 63, 58, 57, 51, 50, 48, 43, 42, 41, 35, 31, 30, 29, 28. Anal. Calcd for C15H21N3O3+1.0H2O: C, 56.68; H, 5.71; N, 15.11. Found: C, 56.73; H, 5.51; N, 14.82.

Workup

  1. customThe reaction was evaporated
  2. additiontreated with methanol
  3. customevaporated to a tan solid, 0.20 g
  4. customThis residue was purified by chromatography (silica gel, dichloromethane and methanol gradient)

Sources & evidence

ORD record
ord-4de21edfd0744706a81b4b66e27b99af
Source dataset
uspto-grants-2012_08
Patent number
US08252793B2

Reaction notes

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