Hydrochloric Acid → HCID 86682753, compound

HRID 1755426Notes

Reaction equation

HRID 1755426 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]3[CH:23]=[C:24]([NH:31][C:32]4[CH:37]=[CH:36][CH:35]=[C:34]([N:38]5[CH2:42][CH2:41][CH2:40][CH:39]5[CH3:43])[N:33]=4)[C:25]4[N:26]([CH:28]=[CH:29][N:30]=4)[N:27]=3)[CH:17]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.[ClH:44]>ClCCl>[ClH:44].[CH3:43][CH:39]1[CH2:40][CH2:41][CH2:42][N:38]1[C:34]1[N:33]=[C:32]([NH:31][C:24]2[C:25]3[N:26]([CH:28]=[CH:29][N:30]=3)[N:27]=[C:22]([C:18]3[CH:19]=[CH:20][CH:21]=[C:16]([CH2:15][NH:14][CH:11]4[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]4)[CH:17]=3)[CH:23]=2)[CH:37]=[CH:36][CH:35]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86682752HCID 86682752, compound

Product 1

HCID 86682753HCID 86682753, compoundYield 109%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl-4-(3-(8-(6-(2-methylpyrrolidin-1-yl)pyridin-2-ylamino)imidazo[1,2-b]pyridazin-6-yl)benzylamino)piperidine-1-carboxylate (35 mg, 0.06 mmol) was dissolved in HCl gas in dichloromethane (5 mL). The solution was stirred at room temperature for 2 h. The solvent was concentrated in vacuo to give N-(6-(2-methylpyrrolidin-1-yl)pyridin-2-yl)-6-(3-((piperidin-4-ylamino)methyl)phenyl)imidazo[1,2-b]pyridazin-8-amine hydrochloride (35 mg, 109%) as a yellow solid. 1H NMR (300 MHz, DMSO+D2O): δ 9.18 (s, 1H), 8.49 (s, 1H), 8.27 (s, 1H), 8.17 (s, 1H), 7.99 (d, 1H, J=7.5 Hz), 7.80 (d, 1H, J=7.5 Hz), 7.68 (t, 1H, J=7.5 Hz), 7.53 (t, 1H, J=7.8 Hz), 6.60 (d, 1H, J=7.5 Hz), 6.19 (d, 1H, J=8.4 Hz), 4.28-4.21 (m, 3H), 3.53-3.38 (m, 5H), 2.95 (t, 2H, J=12.3 Hz), 2.31-2.28 (m, 2H), 2.07-1.68 (m, 6H), 1.06 (d, 3H, J=6.0 Hz). LC/MS: 486 [M+H]+, tR=0.85 min. HPLC: 100% at 214 nm, 99.89% at 254 nm, tR=4.58 min.

Workup

  1. concentrationThe solvent was concentrated in vacuo

Sources & evidence

ORD record
ord-4da6e43f870d431bbe78de6bab78fb7e
Source dataset
uspto-grants-2015_10
Patent number
US09169259B2

Reaction notes

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