Trifluoroacetic acid → HCID 178439555, compound

HRID 2239895Notes

Reaction equation

HRID 2239895 reaction equation
[NH2:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([NH:8][C:9]2[CH:10]=[C:11]([N:21](CC3C=CC(OC)=CC=3)[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:12]3[N:13]([C:15]([C:18]#[C:19][CH3:20])=[CH:16][N:17]=3)[N:14]=2)[CH2:4][CH2:3]1.C(N1CCCC(NC2C=C(N(CC3C=CC(OC)=CC=3)C3C=CC=CC=3)C3N(C(C#N)=CN=3)N=2)C1)C1C=CC=CC=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:1][C@H:2]1[CH2:3][CH2:4][C@H:5]([NH:8][C:9]2[CH:10]=[C:11]([NH:21][C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:12]3[N:13]([C:15]([C:18]#[C:19][CH3:20])=[CH:16][N:17]=3)[N:14]=2)[CH2:6][CH2:7]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 68481210HCID 68481210, compoundHCID 178439556HCID 178439556, compound

Product 1

HCID 178439555HCID 178439555, compoundYield 5.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 2 dram vial was added crude N6-((trans)-4-aminocyclohexyl)-N8-(4-methoxybenzyl)-N8-phenyl-3-(prop-1-ynyl)imidazo[1,2-b]pyridazine-6,8-diamine (0.065 g, 0.13 mmol) from (1b) and a 1:1 mixture of TFA and CH2Cl2 (2 ml). The reaction was stirred for 2 hours, concentrated, diluted with MeOH and purified by preparative HPLC to provide the titled compound (0.0025 g, 5%) as a TFA salt. 1H NMR (400 MHz, MeOD) δ ppm 7.44 (2H, dd, 8 Hz), 7.33 (2H, d, 8 Hz), 7.18-7.26 (1H, m), 7.18-7.25 (2H, m), 6.39 (1H, s), 3.68-3.82 (1H, m), 3.06-3.21 (1H, m), 2.23-2.35 (2H, m), 2.18 (3H, s), 1.46-1.62 (2H, m), 1.25-1.41 (2H, m). LC/MS, m/z 361 (M+1). HPLC Rt, 2.30 min. Waters Sunfire C18 column (4.6×50 mm). 0%-100% B. Solvent B: (90% MeOH, 10% H2O, 0.1% TFA). Solvent A: (10% MeOH, 90% H2O, 0.1% TFA). Gradient, start % B=0, final % B=100, gradient time 4 min, hold at 100% B 1 min, flow rate 4 mL/min.

Workup

  1. concentrationconcentrated
  2. additiondiluted with MeOH
  3. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-9bd52a3a00fe4457ae03d56d6576700b
Source dataset
uspto-grants-2010_05
Patent number
US07723336B2

Reaction notes

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