Trifluoroacetic acid → HCID 59304362, compound

HRID 2241354Notes

Reaction equation

HRID 2241354 reaction equation
COC1C=CC(C[N:8]2[C:12]3=[N:13][CH:14]=[CH:15][C:16]([O:17][C:18]4[CH:23]=[CH:22][C:21]([NH:24][C:25]([C:27]5[C:28](=[O:40])[N:29]([C:33]6[CH:38]=[CH:37][C:36]([F:39])=[CH:35][CH:34]=6)[N:30]=[CH:31][CH:32]=5)=[O:26])=[CH:20][C:19]=4[F:41])=[C:11]3[C:10]([N:42]3[CH2:48][CH2:47][CH2:46][NH:45][CH2:44][CH2:43]3)=[N:9]2)=CC=1.C(O)(C(F)(F)F)=O>>[N:42]1([C:10]2[C:11]3[C:12](=[N:13][CH:14]=[CH:15][C:16]=3[O:17][C:18]3[CH:23]=[CH:22][C:21]([NH:24][C:25]([C:27]4[C:28](=[O:40])[N:29]([C:33]5[CH:34]=[CH:35][C:36]([F:39])=[CH:37][CH:38]=5)[N:30]=[CH:31][CH:32]=4)=[O:26])=[CH:20][C:19]=3[F:41])[NH:8][N:9]=2)[CH2:48][CH2:47][CH2:46][NH:45][CH2:44][CH2:43]1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68515987HCID 68515987, compound

Product 1

HCID 59304362HCID 59304362, compoundYield 1.8%

Conditions

Temperature
80 °C

Procedure

A 100 mL round-bottomed flask was charged with N-(4-(1-(4-methoxybenzyl)-3-(1,4-diazepan-1-yl)-1H-pyrazolo[3,4-b]pyridin-4-yloxy)-3-fluorophenyl)-2-(4-fluorophenyl)-3-oxo-2,3-dihydropyridazine-4-carboxamide (60.7 mg, 0.0894 mmol) and CF3COOH (5 mL). The reaction mixture was stirred at 80° C. overnight. The solvent was removed and the residue was purified by silica gel chromatography (DCM/7 M NH3 in MeOH from 50/1 to 10/1, v/v) to afford product, which was further purified by preparative HPLC to afford the product (0.9 mg, 1.28%). LRMS (APCI pos): >99% purity, 254 nm, m/e 559 (M+1). 1H NMR (400 MHz, CD3OD δ 8.34 (m, 2H), 8.22 (d, 1H), 8.07 (d, 1H), 7.67 (m, 2H), 7.52 (d, 1H), 7.43 (t, 1H), 7.30 (m, 2H), 6.27 (d, 1H), 3.91 (m, 2H), 3.75 (m, 2H), 3.48 (m, 2H), 3.39 (m, 2H), 2.23 (m, 2H).

Workup

  1. customThe solvent was removed
  2. customthe residue was purified by silica gel chromatography (DCM/7 M NH3 in MeOH from 50/1 to 10/1
  3. customv/v) to afford product, which
  4. customwas further purified by preparative HPLC

Sources & evidence

ORD record
ord-2fd1e02de9e846309044df1f3dadf318
Source dataset
uspto-grants-2010_05
Patent number
US07723330B2

Reaction notes

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