Sodium Carbonate → HCID 44219346, compound

HRID 1928830Notes

Reaction equation

HRID 1928830 reaction equation
[C@H:1]1([NH:10][C:11]2[CH:20]=[CH:19][C:18]3[C:13](=[CH:14][CH:15]=[C:16]([NH:21][C:22]([NH:24][CH:25]4[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]4)=[O:23])[CH:17]=3)[N:12]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.Cl[CH2:32][C:33]([N:35]([CH3:37])[CH3:36])=[O:34].C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O>[C@H:1]1([NH:10][C:11]2[CH:20]=[CH:19][C:18]3[C:13](=[CH:14][CH:15]=[C:16]([NH:21][C:22](=[O:23])[NH:24][CH:25]4[CH2:30][CH2:29][N:28]([CH2:32][C:33]([N:35]([CH3:37])[CH3:36])=[O:34])[CH2:27][CH2:26]4)[CH:17]=3)[N:12]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 758862-chloro-N,N-dimethylacetamideHCID 44217941HCID 44217941, compound

Product 1

HCID 44219346HCID 44219346, compoundYield 90.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-[2-((R)-Indan-1-ylamino)-quinolin-6-yl]-3-piperidin-4-yl-urea (0.05 g, 0.12 mmol), 2-chloro-N,N-dimethylacetamide (0.023 mg, 0.18 mmol) and sodium carbonate (0.02 g, 0.18 mmol) were stirred at ambient temperature for 16 h in N,N-dimethylformamide (3 mL). The reaction mixture was evaporated. The residue was taken up in dimethylsulfoxide (1 mL) and subjected to preparative HPLC to yield the title compound (0.053 g, 87%) as a yellow oil; MS: m/e=487.8 (M+H+).

Workup

  1. customThe reaction mixture was evaporated

Sources & evidence

ORD record
ord-b5da94124c75487e90ee772c418c8fa5
Source dataset
uspto-grants-2012_05
Patent number
US08183380B2

Reaction notes

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