Trifluoroacetic acid → HCID 22224732, compound

HRID 1635359Notes

Reaction equation

HRID 1635359 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).

Sources & evidence

ORD record
ord-957b9fe9921c40599f356a5cf527aa1b
Source dataset
uspto-grants-2003_01
Patent number
US06509328B1

Reaction notes

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