Formaldehyde → HCID 11394517, compound

HRID 422237Notes

Reaction equation

HRID 422237 reaction equation
[CH2:1]([NH:7][CH:8]1[C:16]2[C:11](=[CH:12][C:13]([O:17][C:18]3[CH:26]=[CH:25][C:21]([C:22]([NH2:24])=[O:23])=[CH:20][N:19]=3)=[CH:14][CH:15]=2)[CH2:10][CH2:9]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].C=O.[BH3-][C:30]#N.[Na+]>>[CH2:1]([N:7]([CH3:30])[CH:8]1[C:16]2[C:11](=[CH:12][C:13]([O:17][C:18]3[CH:26]=[CH:25][C:21]([C:22]([NH2:24])=[O:23])=[CH:20][N:19]=3)=[CH:14][CH:15]=2)[CH2:10][CH2:9]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

4

Reactant 3

HCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 11360176HCID 11360176, compound

Product 1

HCID 11394517HCID 11394517, compoundYield 73.6%

Procedure

Using a method similar to Example 13, using 6-(1-hexylamino-indan-5-yloxy)-nicotinamide (example 12, 490 mg, 1.38 mmol), paraformaldehyde (443 mg), and NaBH3CN (261 mg, 4.16 mmol) gives the title compound (373 mg) as a light yellow solid. Mass spectrum (ion spray): m/z=368 (M+1); 1HNMR (CDCl3): 8.59 (s, 1H), 8.16 (d, 1H), 7.38 (d, 1H), 6.98-6.93 (m, 3H), 5.89 (br. s, 2H), 4.42 (t, 1H), 2.97-2.78 (m, 2H), 2.40 (m, 2H), 2.22 (s, 3H), 2.08 (m, 2H), 1.51 (m, 2H), 1.36-1.22 (m, 6H), 0.88 (t, 3H).

Sources & evidence

ORD record
ord-801c1e66a1fd479cb0a4633a4c5cb23b
Source dataset
uspto-grants-2012_01
Patent number
US08101638B2

Reaction notes

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