Formaldehyde → HCID 86716119, compound

HRID 627555Notes

Reaction equation

HRID 627555 reaction equation
[Cl:1][C:2]1[C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:10]([Cl:18])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:19]([CH:27]3[CH2:32][CH2:31][CH2:30][NH:29][CH2:28]3)([C:21]3[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=3)[OH:20])[CH:8]=2)[N:3]=1.[C:33]([OH:39])([C:35]([F:38])([F:37])[F:36])=[O:34].C=O.O.[BH3-]C#N.[Na+]>CO>[Cl:1][C:2]1[C:11]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[C:10]([Cl:18])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:19]([CH:27]3[CH2:32][CH2:31][CH2:30][N:29]([CH3:33])[CH2:28]3)([C:21]3[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=3)[OH:20])[CH:8]=2)[N:3]=1.[C:33]([OH:39])([C:35]([F:38])([F:37])[F:36])=[O:34]

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 962WaterHCID 5003444Sodium cyanoborohydrideHCID 86716116HCID 86716116, compound

Product 1

HCID 86716119HCID 86716119, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of (2,4-dichloro-3-phenylquinolin-6-yl)(piperidin-3-yl)pyridin-3-ylmethanol•TFA (15 mg, 0.022 mmol, Example 93), 37% formaldehyde in water (0.010 mL, 0.13 mmol) and MeOH (1 mL) was added NaBH3CN (4.0 mg, 0.064 mmol). The mixture was stirred overnight and concentrated. The residue was purified by reverse phase HPLC (water/acetonitrile/0.1% TFA) to provide the title compound as a white solid. 1H NMR (400 MHz, MeOH-d4) δ 8.95 (s, 1H), 8.54-8.68 (m, 2H), 8.41 (d, J=7.58 Hz, 1H), 7.96-8.13 (m, 2H), 7.72 (dd, J=5.14, 7.58 Hz, 1H), 7.53 (d, J=7.09 Hz, 3H), 7.33 (d, J=6.85 Hz, 2H), 3.48-3.64 (m, 1H), 3.10-3.21 (m, 1H), 2.96-3.10 (m, 1H), 2.83-2.97 (m, 1H), 2.80 (s, 3H), 2.66 (s, 1H), 2.01-2.13 (m, 1H), 1.82-2.01 (m, 1H), 1.54-1.82 (m, 2H); MS m/e 478.0 [M+H]+.

Workup

  1. concentrationconcentrated
  2. customThe residue was purified by reverse phase HPLC (water/acetonitrile/0.1% TFA)

Sources & evidence

ORD record
ord-dd0f4f9ce3924639b6f18d339a96cc16
Source dataset
uspto-grants-2016_04
Patent number
US09309222B2

Reaction notes

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