Acetic Acid → HCID 86682752, compound

HRID 1755425Notes

Reaction equation

HRID 1755425 reaction equation
[NH2:1][CH2:2][C:3]1[CH:4]=[C:5]([C:9]2[CH:10]=[C:11]([NH:18][C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([N:25]4[CH2:29][CH2:28][CH2:27][CH:26]4[CH3:30])[N:20]=3)[C:12]3[N:13]([CH:15]=[CH:16][N:17]=3)[N:14]=2)[CH:6]=[CH:7][CH:8]=1.O=[C:32]1[CH2:37][CH2:36][N:35]([C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[CH2:34][CH2:33]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].CC(O)=O>ClCCl>[CH3:30][CH:26]1[CH2:27][CH2:28][CH2:29][N:25]1[C:21]1[N:20]=[C:19]([NH:18][C:11]2[C:12]3[N:13]([CH:15]=[CH:16][N:17]=3)[N:14]=[C:9]([C:5]3[CH:4]=[C:3]([CH:8]=[CH:7][CH:6]=3)[CH2:2][NH:1][CH:32]3[CH2:37][CH2:36][N:35]([C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[CH2:34][CH2:33]3)[CH:10]=2)[CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 5049666Sodium triacetoxyborohydrideHCID 71462533HCID 71462533, compound

Product 1

HCID 86682752HCID 86682752, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-(3-(aminomethyl)phenyl)-N-(6-(2-methylpyrrolidin-1-yl)pyridin-2-yl)imidazo[1,2-b]pyridazin-8-amine (50 mg, 1.52 mmol), tert-butyl 4-oxopiperidine-1-carboxylate (38 mg, 0.188 mmol) and NaBH(OAc)3 (80 mg, 0.375 mmol) in dichloromethane (5 mL) was added HOAc (12 mg). The mixture was stirred at room temperature for 3 h. The solvent was concentrated in vacuo. The residue was purified by chromatography (silica, EtOAc) to give 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, 48%) as a yellow oil. LC/MS: 583.3 [M+H]+, tR=1.52 min.

Workup

  1. concentrationThe solvent was concentrated in vacuo
  2. customThe residue was purified by chromatography (silica, EtOAc)

Sources & evidence

ORD record
ord-047058d15eb0482585d2a582e1e824b4
Source dataset
uspto-grants-2015_10
Patent number
US09169259B2

Reaction notes

Loading…