Formaldehyde → HCID 59392825, compound

HRID 216739Notes

Reaction equation

HRID 216739 reaction equation
[O:1]=[S:2]1(=[O:39])[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[C:14]([F:15])=[CH:13][C:12]([C:16]3[CH:17]=[CH:18][CH:19]=[C:20]4[C:25]=3[N:24]=[C:23]([C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([N:32]5[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]5)[CH:27]=3)[CH:22]=[N:21]4)=[CH:11][C:10]=2[F:38])[CH2:4][CH2:3]1.C=O.[BH3-][C:43]#N.[Na+]>CO.C(Cl)Cl>[O:39]=[S:2]1(=[O:1])[CH2:3][CH2:4][N:5]([CH2:8][C:9]2[C:14]([F:15])=[CH:13][C:12]([C:16]3[CH:17]=[CH:18][CH:19]=[C:20]4[C:25]=3[N:24]=[C:23]([C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([N:32]5[CH2:37][CH2:36][N:35]([CH3:43])[CH2:34][CH2:33]5)[CH:27]=3)[CH:22]=[N:21]4)=[CH:11][C:10]=2[F:38])[CH2:6][CH2:7]1

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 59392769HCID 59392769, compound

Product 1

HCID 59392825HCID 59392825, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 8-[4-(1,1-Dioxido-thiomorpholin-4-ylmethyl)-3,5-difluoro-phenyl]-2-(3-piperazin-1-yl-phenyl)-quinoxaline (as obtained in example 169, 79 mg, 0.137 mmol) in MeOH (3 ml) and CH2Cl2 (1.5 ml) is treated with HCHO (41 μl, 0.550 mmol, 37% in H2O/MeOH 9:1) and NaBH3CN (35 mg, 0.546 mmol) at RT for 2 h. The reaction mixture is concentrated under reduced pressure. The residue is purified by reverse phase prep-HPLC (Waters) to afford the title compound as a yellow solid.

Workup

  1. concentrationThe reaction mixture is concentrated under reduced pressure
  2. customThe residue is purified by reverse phase prep-HPLC (Waters)

Sources & evidence

ORD record
ord-2e3633a0f4744f669fdf4ada2294da4b
Source dataset
uspto-grants-2012_06
Patent number
US08193189B2

Reaction notes

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