Trifluoroacetic acid → HCID 22224732, compound

HRID 859487Notes

Reaction equation

HRID 859487 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]#[C:15][C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=2)=[CH:10][C:9]=1[NH2:23])(C)(C)C.CC1(C)O[C:30]([C:32]2[CH:33]=[C:34]([CH:37]=[CH:38][CH:39]=2)[C:35]#[N:36])=[CH:29][C:28](=[O:40])O1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:22][C:19]1[CH:18]=[CH:17][C:16]([C:15]#[C:14][C:11]2[CH:12]=[CH:13][C:8]3[N:7]=[C:30]([C:32]4[CH:33]=[C:34]([CH:37]=[CH:38][CH:39]=4)[C:35]#[N:36])[CH2:29][C:28](=[O:40])[NH:23][C:9]=3[CH:10]=2)=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 117363373-(2,2-Dimethyl-6-oxo-6H-[1,3]dioxin-4-yl)-benzonitrileHCID 69592820HCID 69592820, compound

Product 1

HCID 22224732HCID 22224732, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Prepared from [2-amino-4-(4-chloro-phenylethynyl)-phenyl]-carbamic acid tert.-butyl ester (Example G13) (187 mg, 0.5 mmol) and 3-(2,2-dimethyl-6-oxo-6H-[1,3]dioxin-4-yl)-benzonitrile (Example J4) (184 mg, 0.6 mmol) according to the general procedure K. The obtained material (234 mg) was deprotected and cyclized by treatment with TFA in CH2Cl2 according to the general procedure M. Obtained as a light yellow powder (93 mg). MS (EI) 395 (M+) and 397 [(M+2)+]; mp 237–240° C. (dec.).

Sources & evidence

ORD record
ord-4766fbffd0664c2baec7452f7ebe54ff
Source dataset
uspto-grants-2006_12
Patent number
US07151098B2

Reaction notes

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