Dichloromethane → HCID 51348456, compound

HRID 1405943Notes

Reaction equation

HRID 1405943 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].C(N(CC)CC)C.Cl.[CH3:43][S:44][CH2:45][CH2:46][NH2:47].ClCCl>ClCCl.CO>[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:47][CH2:46][CH2:45][S:44][CH3:43])=[CH:24][CH:23]=4)[CH:20]=3)[N:15]=[CH:14][N:13]=2)=[CH:9][C:8]=1[Cl:31]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 11181296(5-(4-(4-((3-Fluorobenzyl)oxy)-3-chloroanilino)-6-quinazolinyl)-2-furancarboxaldehydeHCID 227227922-(Methylsulfanyl)ethan-1-amine--hydrogen chloride (1/1)

Product 1

HCID 51348456HCID 51348456, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

10.0 g of compound 5-(4-(4-(3-fluorobenzyloxy)-3-chloroanilino)-6-quinazolinyl)furan-2-formaldehyde was dissolved in the mixture of dichloromethane/methanol (3:1). The mixture was added with 4.3 g of triethylamine, stirred for 10 min, added with 6.9 g of 2-methylthioethylamine hydrochloride, and stirred at room temperature. Upon consumption of the starting materials detected by TLC, 2.4 g of sodium borohydride was added in batches under ice-bath. Upon the end of reaction detected by TLC, dichloromethane (q.s.) was added. The mixture was washed with saturated ammonium chloride and then with saturated sodium chloride, dried over anhydrous sodium sulfate, and subjected to a column chromatography to obtain 6.5 g of yellow solid, yield 56%.

Workup

  1. stirringstirred at room temperature
  2. customUpon consumption of the starting materials
  3. additionwas added in batches under ice-bath
  4. customUpon the end of reaction
  5. additionwas added
  6. washThe mixture was washed with saturated ammonium chloride
  7. dry with materialwith saturated sodium chloride, dried over anhydrous sodium sulfate

Sources & evidence

ORD record
ord-2312e9b02f144bfc9175e13ac8e7a7e6
Source dataset
uspto-grants-2014_12
Patent number
US08916574B2

Reaction notes

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