Trifluoroacetic acid → HCID 178507238, compound

HRID 1615339Notes

Reaction equation

HRID 1615339 reaction equation
[O:1]=[C:2]1[NH:3][C:4]2[C:9](/[C:10]/1=[CH:11]\[C:12]1[CH:20]=[C:19]3[C:15]([C:16](/[CH:21]=[CH:22]/[C:23]4[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=4)=[N:17][NH:18]3)=[CH:14][CH:13]=1)=[CH:8][C:7]([NH:29]C(=O)OC(C)(C)C)=[CH:6][CH:5]=2.[F:37][C:38]([F:43])([F:42])[C:39]([OH:41])=[O:40]>C(Cl)Cl>[F:37][C:38]([F:43])([F:42])[C:39]([OH:41])=[O:40].[F:37][C:38]([F:43])([F:42])[C:39]([OH:41])=[O:40].[NH2:29][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[NH:3][C:2](=[O:1])/[C:10]/2=[CH:11]/[C:12]1[CH:20]=[C:19]2[C:15]([C:16](/[CH:21]=[CH:22]/[C:23]3[CH:24]=[CH:25][N:26]=[CH:27][CH:28]=3)=[N:17][NH:18]2)=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178452630HCID 178452630, compound

Product 1

HCID 178507238HCID 178507238, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl(E)-2-oxo-3-((3-((E)-2-(pyridin-4-yl)vinyl)-1H-indazol-6-yl)-methyl-ene)indolin-5-ylcarbamate (13 mg, 0.027 mmol) was dissolved into CH2Cl2 (1.0 mL) and then trifluoroacetic acid (0.1 mL) was added and the reaction stirred for 1 hour. The solvent was removed and the residue titurated with ether/EtOAc to give after drying 4.6 mg, 29% of the title compound as an orange powder. 1H NMR (400 MHz, CD3OD) δ 8.68 (d, J=5.8 Hz, 2H), 8.31 (d, J=8.7 Hz, 1H), 8.21-8.12 (m, 3H), 7.97 (s, 1H), 7.88 (s, 1H), 7.70 (d, J=16.8 Hz, 1H), 7.62-7.57 (m, 2H), 7.18 (d, J=8.8 Hz, 1H), 6.99 (d, J=8.6 Hz, 1H); MS ESI 380.1 [M+H]+, calcd for [C23H17N5O+H]+ 380.15.

Workup

  1. customThe solvent was removed
  2. customto give
  3. dry with materialafter drying 4.6 mg, 29% of the title compound as an orange powder

Sources & evidence

ORD record
ord-bce5e83a0be443c6b80790a0b41b8327
Source dataset
uspto-grants-2014_07
Patent number
US08765748B2

Reaction notes

Loading…