Formaldehyde → 6-[5-(4-Chloro-phenyl)-pyridin-2-ylethynyl]-1-methyl-2-pyrrolidin-1-ylmethyl-1,2,3,4-tetrahydro-quinoline

HRID 1916690Notes

Reaction equation

HRID 1916690 reaction equation
C=O.[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[CH:12][C:13]([C:16]#[C:17][C:18]3[CH:19]=[C:20]4[C:25](=[CH:26][CH:27]=3)[NH:24][CH:23]([CH2:28][N:29]3[CH2:33][CH2:32][CH2:31][CH2:30]3)[CH2:22][CH2:21]4)=[N:14][CH:15]=2)=[CH:6][CH:5]=1.[C:34]([BH3-])#N.C1(C)C(S(O)(=O)=O)=CC=CC=1>C1COCC1.C(O)(=O)C>[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[CH:12][C:13]([C:16]#[C:17][C:18]3[CH:19]=[C:20]4[C:25](=[CH:26][CH:27]=3)[N:24]([CH3:34])[CH:23]([CH2:28][N:29]3[CH2:30][CH2:31][CH2:32][CH2:33]3)[CH2:22][CH2:21]4)=[N:14][CH:15]=2)=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 712FormaldehydeHCID 69252-Methylbenzenesulfonic acidHCID 498716Cyano-borohydrideHCID 117432956-[5-(4-Chloro-phenyl)-pyridin-2-ylethynyl]-2-pyrrolidin-1-ylmethyl-1,2,3,4-tetrahydro-quinoline

Product 1

HCID 598358636-[5-(4-Chloro-phenyl)-pyridin-2-ylethynyl]-1-methyl-2-pyrrolidin-1-ylmethyl-1,2,3,4-tetrahydro-quinoline

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

37 mg (1.23 mmol) paraformaldehyde in 1.8 mL THF are added to a solution of 350 mg (0.82 mmol) 6-[5-(4-chloro-phenyl)-pyridin-2-ylethynyl]-2-pyrrolidin-1-ylmethyl-1,2,3,4-tetrahydro-quinoline (see Example 3.46) in 1.6 mL THF. 0.24 mL acetic acid and 1.2 mL THF are added to this mixture. Finally, 1.00 g (2.05 mmol) cyanoborohydride resin (macroporous polystyrene, load: 2.04 mmol/g) are added and the mixture is stirred for 16 h at RT. After filtration the filtrate is combined with 1.50 g (2.15 mmol) toluenesulphonic acid resin (macroporous polystyrene, load: 1.43 mmol/g), shaken for 30 min and suction filtered. The solvent is eliminated i.vac. and purification is carried out by column chromatography using HPLC-MS.

Workup

  1. filtrationAfter filtration the filtrate
  2. stirringshaken for 30 min
  3. filtrationsuction filtered
  4. customand purification

Sources & evidence

ORD record
ord-42c3bac3f94e4caca373a8af6458197d
Source dataset
uspto-grants-2013_12
Patent number
US08618132B2

Reaction notes

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