Trifluoroacetic acid → HCID 44608430, compound

HRID 1963790Notes

Reaction equation

[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:17]=[C:16]3[C:11]([N:12]=[CH:13][C:14]([NH:18][CH2:19][CH:20]4[CH2:25][CH2:24][CH2:23][N:22](C(OC(C)(C)C)=O)[CH2:21]4)=[N:15]3)=[CH:10][CH:9]=2)=[CH:4][C:3]=1[NH:33][S:34]([C:37]1[CH:42]=[CH:41][C:40]([F:43])=[CH:39][CH:38]=1)(=[O:36])=[O:35].C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:1][C:2]1[C:3]([NH:33][S:34]([C:37]2[CH:38]=[CH:39][C:40]([F:43])=[CH:41][CH:42]=2)(=[O:35])=[O:36])=[CH:4][C:5]([C:8]2[CH:17]=[C:16]3[C:11](=[CH:10][CH:9]=2)[N:12]=[CH:13][C:14]([NH:18][CH2:19][CH:20]2[CH2:25][CH2:24][CH2:23][NH:22][CH2:21]2)=[N:15]3)=[CH:6][N:7]=1

Participants

Conditions

Temperature: 23 °C

Procedure

(Some starting materials may be obtained from Asta Tech, Inc., Princeton, N.J.) To a solution of tert-butyl 3-((7-(6-chloro-5-(4-fluorophenylsulfonamido)pyridin-3-yl)quinoxalin-2-ylamino)methyl)piperidine-1-carboxylate (5 mg, 8 μmol) in DCM (1 mL) was added TFA (1 mL) and the reaction was stirred at 23° C. for 15 min. The reaction was then concentrated in vacuo and coevaporated with DCM (3×; 1 ml) to give the desired product as a yellow film. MS (ESI pos. ion) m/z calc'd for C25H24ClFN6O2S: 526.1; found 527.0. 1H NMR (300 MHz, CDCl3) δ ppm 1.23-1.38 (m, 2 H) 1.78 (m, 1 H) 1.89 (m, 2 H) 2.22 (br. s., 1 H) 2.66 (t, J=11.84 Hz, 1 H) 2.79 (d, J=3.07 Hz, 1 H) 3.36-3.52 (m, 3 H) 7.05-7.12 (m, 2 H) 7.48 (dd, J=8.48, 2.05 Hz, 1 H) 7.71-7.88 (m, 4 H) 8.19-8.23 (m, 2 H) 8.38-8.41 (m, 1 H)

Workup

concentrationThe reaction was then concentrated in vacuo

Sources & evidence

ORD record: ord-a01bd78bbe0b47ac821a5afe7e45db89
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08415376B2

Reaction notes

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