Trifluoroacetic acid → HCID 78323679, compound

HRID 2170150Notes

Reaction equation

C([NH:5][S:6]([C:9]1[S:10][CH:11]=[C:12]([C:14]2[N:19]=[C:18]([NH:20][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=3)[C:17]3=[C:28]([C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)[CH:29]=[CH:30][N:16]3[N:15]=2)[N:13]=1)(=[O:8])=[O:7])(C)(C)C.C(O)(C(F)(F)F)=O>>[C:31]1([C:28]2[CH:29]=[CH:30][N:16]3[C:17]=2[C:18]([NH:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=2)=[N:19][C:14]([C:12]2[N:13]=[C:9]([S:6]([NH2:5])(=[O:7])=[O:8])[S:10][CH:11]=2)=[N:15]3)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 90386205HCID 90386205, compound

Product 1

HCID 78323679HCID 78323679, compoundYield 26%

Procedure

N-(tert-Butyl)-4-(5-phenyl-4-((pyridin-2-ylmethyl)amino)pyrrolo[2,1-f][1,2,4]triazin-2-yl)thiazole-2-sulfonamide (40.0 mg, 0.0770 mmol) and TFA (3 mL) were stirred at ambient temperature for 14 h. The excess TFA was evaporated under reduced pressure and the residue purified by preparative HPLC (Condition B-33 as described in general methods) to obtain 4-(5-phenyl-4-((pyridin-2-ylmethyl)amino)pyrrolo[2,1-f][1,2,4]triazin-2-yl)thiazole-2-sulfonamide (9.00 mg, 26.0%). LCMS Condition B-13: retention time 1.94 min, [M+1]=464.0. HPLC Condition B-32: retention time 7.06 min, Purity 97.62%. 1H NMR (400 MHz, DMSO-d6): δ ppm 4.91 (d, J=4.4 Hz, 2H), 6.82 (d, J=2.8 Hz, 1H), 7.27-7.31 (m, 2H), 7.43-7.61 (m, 6H), 7.79 (dt, J=2.0 Hz, J=8.0 Hz, 1H), 7.90 (d, J=2.8 Hz, 1H), 8.24 (s, 2H), 8.39-8.40 (m, 1H), 8.63 (s, 1H).

Workup

customThe excess TFA was evaporated under reduced pressure
customthe residue purified by preparative HPLC (Condition B-33 as described in general methods)

Sources & evidence

ORD record: ord-2b268e5b67d645eba22883aef71f55e2
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09050345B2

Reaction notes

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