Trifluoroacetic acid → Trifluoroacetic acid

HRID 657684Notes

Reaction equation

HRID 657684 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][C:10]2[C:11]([CH3:20])=[N:12][C:13]3[N:14]([N:17]=[CH:18][N:19]=3)[C:15]=2[NH2:16])=[CH:4][CH:3]=1.[Cl:21][C:22]1[CH:23]=[C:24]([N:28]=[C:29]=[O:30])[CH:25]=[CH:26][CH:27]=1.C(N(CC)CC)C.[F:38][C:39]([F:44])([F:43])[C:40]([OH:42])=[O:41]>CC#N>[F:38][C:39]([F:44])([F:43])[C:40]([OH:42])=[O:41].[NH2:16][C:15]1[N:14]2[N:17]=[CH:18][N:19]=[C:13]2[N:12]=[C:11]([CH3:20])[C:10]=1[C:9]#[C:8][C:5]1[CH:6]=[CH:7][C:2]([NH:1][C:29]([NH:28][C:24]2[CH:25]=[CH:26][CH:27]=[C:22]([Cl:21])[CH:23]=2)=[O:30])=[CH:3][CH:4]=1

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 17968Benzene, 1-chloro-3-isocyanato-HCID 25105969HCID 25105969, compound

Product 2

HCID 6422Trifluoroacetic acidYield 17.3%HCID 25106032HCID 25106032, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a stirred solution of Example 1 (10 mg, 0.038 mmol) in 1.0 mL of CH3CN was added 3-chloro-phenyl isocyanate (6.4 mg, 0.046 mmol) and triethylamine (8 μL, 0.057 mmol). The resulting mixture was stirred for over night at room temperature. The resulting mixture was purified by reverse phase HPLC (C-18 column, eluting with a 5-100% CH3CN gradient in 0.1% trifluoroacetic acid) to the title compound as its trifluoroacetic acid salt (3.5 mg, 17.3% yield). MS (ESI) m/z 416, 418 (M+H)+.

Workup

  1. customThe resulting mixture was purified by reverse phase HPLC (C-18 column

Sources & evidence

ORD record
ord-6c31a3ee987a49778ddee354820c9dd8
Source dataset
uspto-grants-2011_12
Patent number
US08076344B2

Reaction notes

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