Acetic Acid → HCID 71526442, compound

HRID 1755393Notes

Reaction equation

HRID 1755393 reaction equation
[CH3:1][CH:2]1[CH2:6][CH2:5][CH2:4][N:3]1[C:7]1[N:12]=[C:11]([NH:13][C:14]2[C:15]3[N:16]([CH:28]=[CH:29][N:30]=3)[N:17]=[C:18]([C:20]3[CH:21]=[C:22]([CH:25]=[CH:26][CH:27]=3)[CH:23]=O)[CH:19]=2)[CH:10]=[CH:9][CH:8]=1.[NH:31]1[CH2:35][CH2:34][CH2:33][CH2:32]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].CC(O)=O>ClCCCl>[CH3:1][CH:2]1[CH2:6][CH2:5][CH2:4][N:3]1[C:7]1[N:12]=[C:11]([NH:13][C:14]2[C:15]3[N:16]([CH:28]=[CH:29][N:30]=3)[N:17]=[C:18]([C:20]3[CH:27]=[CH:26][CH:25]=[C:22]([CH2:23][N:31]4[CH2:35][CH2:34][CH2:33][CH2:32]4)[CH:21]=3)[CH:19]=2)[CH:10]=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 31268PyrrolidineHCID 5049666Sodium triacetoxyborohydrideHCID 86682738HCID 86682738, compound

Product 1

HCID 71526442HCID 71526442, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

3-(8-(6-(2-methylpyrrolidin-1-yl)pyridin-2-ylamino)imidazo[1,2-b]pyridazin-6-yl)benzaldehyde (70 mg, 0.175 mmol) and pyrrolidine (14 mg, 0.194 mmol) were dissolved in 1,2-dichloroethane (10 mL), stirred for 1 h, then sodium triacetoxyborohydride (111 mg, 0.525 mmol) was added followed by AcOH (0.2 mL). After 15 h, the solvent was removed and the residue purified by chromatography (silica gel, dichloromethane/methanol 90:1) to give N-(6-(2-methylpyrrolidin-1-yl)pyridin-2-yl)-6-(3-(pyrrolidin-1-ylmethyl)phenyl)imidazo[1,2-b]pyridazin-8-amine (18 mg, 23%) as an orange solid. 1H NMR (300 MHz, CD3OD): δ 8.70 (s, 1H), 8.05 (s, 1H), 7.91-7.85 (m, 2H), 7.59-7.48 (m, 3H), 7.38-7.35 (m, 1H), 6.21 (d, 1H, J=7.5 Hz), 6.01 (d, 1H, J=7.8 Hz), 4.25-4.17 (m, 3H), 3.55 (s, 1H), 3.37-3.44 (m, 1H), 3.17 (brs, 4 h), 2.08-1.97 (m, 7H), 1.72 (brs, 1H), 1.13 (d, 3H, J=4.5 Hz). LC-MS: [M+H]+, 454, tR=1.367 min, HPLC: 99.54% at 214 nm, 99.89% at 254 nm, tR=5.164 min.

Workup

  1. waitAfter 15 h
  2. customthe solvent was removed
  3. customthe residue purified by chromatography (silica gel, dichloromethane/methanol 90:1)

Sources & evidence

ORD record
ord-0f69579ef8ac4ecaa0c47ab412478105
Source dataset
uspto-grants-2015_10
Patent number
US09169259B2

Reaction notes

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