Hydrochloric Acid → HCID 178511633, compound

HRID 2239850Notes

Reaction equation

HRID 2239850 reaction equation
[C:1]1([NH:7][C:8](=[O:41])[NH:9][C:10]2[CH:15]=[CH:14][C:13]([NH:16][C:17]3[C:18]4[N:19]([CH:38]=[CH:39][N:40]=4)[N:20]=[C:21]([NH:23][C@H:24]4[CH2:29][CH2:28][C@H:27]([NH:30]C(=O)OC(C)(C)C)[CH2:26][CH2:25]4)[CH:22]=3)=[CH:12][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl>O1CCOCC1>[NH2:30][C@H:27]1[CH2:26][CH2:25][C@H:24]([NH:23][C:21]2[CH:22]=[C:17]([NH:16][C:13]3[CH:12]=[CH:11][C:10]([NH:9][C:8]([NH:7][C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)=[O:41])=[CH:15][CH:14]=3)[C:18]3[N:19]([CH:38]=[CH:39][N:40]=3)[N:20]=2)[CH2:29][CH2:28]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178454005HCID 178454005, compound

Product 1

HCID 178511633HCID 178511633, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
25 °C

Procedure

In a 2 dram vial was added tert-butyl(trans)-4-(8-(4-(3-phenylureido)phenylamino)imidazo[1,2-b]pyridazin-6-ylamino)cyclohexylcarbamate (0.035 g, 0.06 mmol) from 1d and 4.0M HCl in 1,4 Dioxane (2.0 ml). The reaction was stirred for 1 hr at 25° C., concentrated and then triturated with diethyl ether. The titled compound was filtered off as an HCl salt (0.018 g). 1H NMR (400 MHz, DMSO-D6) δ ppm 9.36 (1H, s), 9.00 (1H, s), 8.88 (1H, s), 8.67 (1H, s), 8.60 (1H, s), 8.10 (1H, s), 7.87 (2H, d, J=5.09 Hz), 7.54 (1H, d, J=9.16 Hz), 7.44 (2H, t, J=7.63 Hz), 7.34 (1H, s), 7.20-7.31 (2H, m), 6.85-7.04 (2H, m), 6.27 (1H, s), 3.38 (1H, s), 3.02 (1H, s), 2.04 (2H, m), 1.95 (2H, m), 1.31-1.53 (2H, m), 1.11-1.29 (2H, m). LC/MS, m/e 457 (M+1). HPLC Rt, 1.93 min. YMC ODSC18 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. customtriturated with diethyl ether
  3. filtrationThe titled compound was filtered off as an HCl salt (0.018 g)
  4. customHPLC Rt, 1.93 min
  5. customB=100, gradient time 4 min
  6. customhold at 100% B 1 min, flow rate 4 mL/min.

Sources & evidence

ORD record
ord-4af429a84a154c8485533d12a3e5162f
Source dataset
uspto-grants-2010_05
Patent number
US07723336B2

Reaction notes

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