Sodium Bicarbonate → HCID 68155180, compound

HRID 1405946Notes

Reaction equation

HRID 1405946 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:32]=[CH:33][CH:34]=1)[CH2:5][O:6][C:7]1[CH:30]=[CH:29][C:10]([NH:11][C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[C:19]([C:22]4[O:26][C:25]([CH:27]=O)=[CH:24][CH:23]=4)[CH:20]=3)[N:15]=[CH:14][N:13]=2)=[CH:9][C:8]=1[Cl:31].Cl.[NH2:36][CH2:37][CH2:38][NH:39][S:40]([CH3:43])(=[O:42])=[O:41].[BH4-].[Na+].C(=O)(O)[O-].[Na+]>ClCCl.CO.C(N(CC)CC)C>[F:1][C:2]1[CH:3]=[C:4]([CH:32]=[CH:33][CH:34]=1)[CH2:5][O:6][C:7]1[CH:30]=[CH:29][C:10]([NH:11][C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[C:19]([C:22]4[O:26][C:25]([CH2:27][NH:36][CH2:37][CH2:38][NH:39][S:40]([CH3:43])(=[O:42])=[O:41])=[CH:24][CH:23]=4)[CH:20]=3)[N:15]=[CH:14][N:13]=2)=[CH:9][C:8]=1[Cl:31]

Participants

7

Reactant 4

HCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 11181296(5-(4-(4-((3-Fluorobenzyl)oxy)-3-chloroanilino)-6-quinazolinyl)-2-furancarboxaldehydeHCID 22609809N-(2-AMINOETHYL)METHANESULFONAMIDE

Product 1

HCID 68155180HCID 68155180, compoundYield 45%

Reagents, catalysts & solvents 2

HCID 8471TriethylamineSolventHCID 21226129Dichloromethane methanolSolvent

Conditions

Temperature
0 °C

Procedure

At room temperature, 10.0 g of compound 5-(4-(4-(3-fluorobenzyloxy)-3-chloroanilino)-6-quinazolinyl)furan-2-formaldehyde, 6.5 g of compound N-(2-aminoethyl)methanesulfonamide hydrochloride, and 14.6 g of triethylamine in the mixture of dichloromethane/methanol (3:1) were stirred overnight, then cooled with ice-bath to 0° C., and 1.4 g of sodium borohydride was added at that temperature. The mixture was warmed to room temperature, stirred overnight, saturated sodium bicarbonate was added to quench the reaction, and extracted with ethyl acetate. The organic phase was washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate, and subjected to a column chromatography to obtain 5.7 g of the desired product, yield 45.0%.

Workup

  1. temperatureThe mixture was warmed to room temperature
  2. stirringstirred overnight
  3. customto quench
  4. customthe reaction
  5. extractionextracted with ethyl acetate
  6. washThe organic phase was washed with saturated sodium chloride solution
  7. dry with materialdried over anhydrous sodium sulfate

Sources & evidence

ORD record
ord-a58cb3cc806146349e7a0c0423e309f7
Source dataset
uspto-grants-2014_12
Patent number
US08916574B2

Reaction notes

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