Formaldehyde → HCID 24782250, compound

HRID 2239381Notes

Reaction equation

HRID 2239381 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:31][C:11]3[C:12](=[O:30])[N:13]([CH2:16][C:17]4[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH2:24][C@H:25]5[CH2:29][CH2:28][CH2:27][NH:26]5)[N:18]=4)[N:14]=[CH:15][C:10]=3[CH:9]=2)=[CH:4][CH:3]=1.[CH2:32]=O>C(Cl)Cl.CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[S:31][C:11]3[C:12](=[O:30])[N:13]([CH2:16][C:17]4[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH2:24][C@H:25]5[CH2:29][CH2:28][CH2:27][N:26]5[CH3:32])[N:18]=4)[N:14]=[CH:15][C:10]=3[CH:9]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 712FormaldehydeHCID 68713332HCID 68713332, compound

Product 1

HCID 24782250HCID 24782250, compound

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

2-(4-Chlorophenyl)-6-({6-[(2R)-pyrrolidin-2-ylmethoxy]pyridin-2-yl}methyl)thieno[2,3-d]pyridazin-7(6H)-one (0.340 g, 0.75 mmol), formaldehyde(aq.) 36% (0.23 mL, 2.25 mmol) and MacroPorous-triacetoxyborohydride (0.88 g, 2.25 mmol) were shaked in DCM/MeOH (1:1, 4 mL) at room temperature for 3 hours. The reaction mixture was filtrated, concentrated in vacuo and purified by flash chromatography using a gradient with EtOAc:MeOH:TEA (1:0.1:0.01) in n-heptane, which gave the product as an solid. Yield: 0.207 g (59%). 1H NMR (400 MHz, CDCl3) δ 8.18 (s, 1H), 7.55-7.61 (m, 2H), 7.37-7.48 (m, 4H), 6.69 (d, 1H, J=7.27 Hz), 6.59 (d, 1H, J=8.26 Hz), 5.45 (s, 2H), 4.21-4.27 (m, 1H), 4.06-4.14 (m, 1H), 2.97-3.04 (m, 1H), 2.41-2.52 (m, 1H), 2.34 (s, 3H), 2.11-2.21 (m, 1H), 1.78-1.91 (m, 1H), 1.54-1.78 (m, 3H). 13C NMR (100 MHz, CDCl3) δ 163.7, 157.4, 153.9, 152.3, 140.3, 139.2, 136.6, 136.0, 133.3, 131.4, 129.8, 128.2, 118.9, 114.3, 110.0, 68.3, 64.4, 57.9, 56.0, 41.8, 28.7, 23.1. MS (ESI+) 467.0 (M+1H+).

Workup

  1. filtrationThe reaction mixture was filtrated
  2. concentrationconcentrated in vacuo
  3. custompurified by flash chromatography

Sources & evidence

ORD record
ord-002a7b412d7d433e8798fc7033c76148
Source dataset
uspto-grants-2010_05
Patent number
US07723331B2

Reaction notes

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