Triethylamine → HCID 49772202, compound

HRID 502232Notes

Reaction equation

HRID 502232 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([CH2:23][CH3:24])[C:10]3[C:15]([C:16]=2[C:17]#[N:18])=[CH:14][CH:13]=[C:12]([O:19][CH:20]([F:22])[F:21])[CH:11]=3)=[CH:4][CH:3]=1.[CH2:25]([N:28]=[C:29]=[O:30])[CH2:26][CH3:27].C(N(CC)CC)C>ClCCCl>[C:17]([C:16]1[C:15]2[C:10](=[CH:11][C:12]([O:19][CH:20]([F:22])[F:21])=[CH:13][CH:14]=2)[N:9]([CH2:23][CH3:24])[C:8]=1[C:5]1[CH:6]=[CH:7][C:2]([NH:1][C:29]([NH:28][CH2:25][CH2:26][CH3:27])=[O:30])=[CH:3][CH:4]=1)#[N:18]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 61033Propyl isocyanateHCID 25051495HCID 25051495, compound

Product 1

HCID 49772202HCID 49772202, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A solution of 2-(4-aminophenyl)-6-difluoromethoxy-1-ethyl-1H-indole-3-carbonitrile (200 mg, 0.611 mmol) in 1,2-dichloroethane (2 mL) is treated with n-propylisocyanate (115 mL, 1.23 mmol) and triethylamine (170 mL, 1.22 mmol). The resulting solution is stirred at ambient temperature for 12 hours, and then concentrated. The residual material is separated by silica gel chromatography (1/2 ethyl acetate-hexane) to afford the title product as a solid.

Workup

  1. concentrationconcentrated
  2. customThe residual material is separated by silica gel chromatography (1/2 ethyl acetate-hexane)

Sources & evidence

ORD record
ord-0ea3ae5e254443b99a1da4cf28b1ca07
Source dataset
uspto-grants-2010_08
Patent number
US07772271B2

Reaction notes

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