Trifluoroacetic acid → HCID 18771667, compound

HRID 460267Notes

Reaction equation

HRID 460267 reaction equation
[CH:1]1([C:4]2[S:5][CH:6]=[C:7]([NH:9][C:10](=[O:34])[NH:11][C:12]3[N:17]=[C:16]([O:18][CH2:19][CH2:20][CH:21]4[CH2:26][CH2:25][N:24](C(OC(C)(C)C)=O)[CH2:23][CH2:22]4)[CH:15]=[CH:14][CH:13]=3)[N:8]=2)[CH2:3][CH2:2]1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH:1]1([C:4]2[S:5][CH:6]=[C:7]([NH:9][C:10]([NH:11][C:12]3[CH:13]=[CH:14][CH:15]=[C:16]([O:18][CH2:19][CH2:20][CH:21]4[CH2:22][CH2:23][NH:24][CH2:25][CH2:26]4)[N:17]=3)=[O:34])[N:8]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 18771670HCID 18771670, compound

Product 1

HCID 18771667HCID 18771667, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a manner similar to that described in Example 2, 2-cyclopropylthiazole-4-carbonylazide (133.0 mg, 0.686 mmol) and tert-butyl 4-[2-(6-amino-pyridin-2-yloxy)-ethyl]-piperidine-1-carboxylate (220.0 mg, 0.686 mmol) were heated in toluene (20 mL) to give the BOC-protected product as a yellow oil. In a similar manner to Example 274, tert-butyl 4-(2-{6-[3-(2-cyclopropyl-thiazol-4-yl)-ureido]-pyridin-2-yloxy}-ethyl)-piperidine-1-carboxylate (7.6 mg, 0.016 mmol) was heated in CH2Cl2 (10 mL) in the presence of TFA (2 mL) to give the product as yellow oil. MS m/z: 388.3 (M+H). Calc'd. for C19H26N5O2S-388.2.

Sources & evidence

ORD record
ord-82d805a0889c4a6281417a16c8a999e9
Source dataset
uspto-grants-2007_03
Patent number
US07196104B2

Reaction notes

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