Formaldehyde → 6-[1-(Methyl-phenethyl-amino)-indan-5-yloxy]-nicotinamide

HRID 422242Notes

Reaction equation

HRID 422242 reaction equation
[CH2:1]([NH:9][CH:10]1[C:18]2[C:13](=[CH:14][C:15]([O:19][C:20]3[CH:28]=[CH:27][C:23]([C:24]([NH2:26])=[O:25])=[CH:22][N:21]=3)=[CH:16][CH:17]=2)[CH2:12][CH2:11]1)[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C=O.[BH3-][C:32]#N.[Na+]>>[CH3:32][N:9]([CH2:1][CH2:2][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1)[CH:10]1[C:18]2[C:13](=[CH:14][C:15]([O:19][C:20]3[CH:28]=[CH:27][C:23]([C:24]([NH2:26])=[O:25])=[CH:22][N:21]=3)=[CH:16][CH:17]=2)[CH2:12][CH2:11]1

Participants

4

Reactant 3

HCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 117731916-(1-Phenethylamino-indan-5-yloxy)-nicotinamide

Product 1

HCID 111766956-[1-(Methyl-phenethyl-amino)-indan-5-yloxy]-nicotinamideYield 91.6%

Procedure

Using a method similar to Example 13, using 6-(1-phenethylamino-indan-5-yloxy)-nicotinamide (example 18, 980 mg, 2.62 mmol), paraformaldehyde (1.03 g), and NaBH3CN (494 mg, 7.87 mmol) gives the title compound (930 mg) as a light yellow solid. Mass spectrum (ion spray): m/z=388 (M+1); 1HNMR (CDCl3): 8.59 (s, 1H), 8.16 (d, 1H), 7.30-7.17 (m, 6H), 6.97-6.91 (m, 3H), 5.79 (br. s, 2H), 4.45 (t, 1H), 2.96-2.74 (m, 4H), 2.68 (m, 2H), 2.33 (s, 3H), 2.09 (m, 2H).

Sources & evidence

ORD record
ord-dedff80eb88048ddb347a741b0705a5e
Source dataset
uspto-grants-2012_01
Patent number
US08101638B2

Reaction notes

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