HCID 86608648, compound → HCID 9885948, compound

HRID 1455062Notes

Reaction equation

HRID 1455062 reaction equation
[N:1]([CH2:4][C:5]([NH:7][C:8]1[CH:9]=[N:10][C:11]([O:14][C:15]2[CH:16]=[C:17]3[C:22](=[CH:23][CH:24]=2)[O:21][CH:20]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:19][CH2:18]3)=[CH:12][CH:13]=1)=[O:6])=[N+]=[N-]>CO.[Pd]>[NH2:1][CH2:4][C:5]([NH:7][C:8]1[CH:9]=[N:10][C:11]([O:14][C:15]2[CH:16]=[C:17]3[C:22](=[CH:23][CH:24]=2)[O:21][CH:20]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH2:19][CH2:18]3)=[CH:12][CH:13]=1)=[O:6]

Participants

4

Reactant 1

HCID 86608648HCID 86608648, compound

Product 1

HCID 9885948HCID 9885948, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

2-Azido-N-[6-(2-phenylchroman-6-yloxy)pyridin-3-yl]acetamide (500 mg) was dissolved in methanol (100 ml) and 10% palladium on charcoal (125 mg) was added. Starting material was hydrogenated for 5 hours at room temperature to give 2-amino-N-[6-(2-phenylchroman-6-yloxy)pyridin-3-yl]acetamide. The product was isolated as its hydrochloride salt. 1H-NMR (400 MHz; d6-DMSO) δ: 10.7 (s, 1H), 8.35 (d, 1H, J 2.6 Hz), 8.17 (bs, 3H), 8.01 (dd, 1H, J 2.6, 8.9 Hz), 7.47-7.32 (m, 51), 7.00 (d, 1H, J 8.9 Hz), 6.89-6.86 (m, 3H), 5.12 (dd, 1H, J 1.90, 10.1 Hz), 3.79 (q, 2H, J 5.6 Hz), 3.01-2.92 (m, 1H), 2.74-2.70 (m, 1H), 2.20-2.15 (m, 1H), 2.05-1.94 (m, 1H).

Sources & evidence

ORD record
ord-c82e553e9dec405ab7f95b8e0ed523f1
Source dataset
uspto-grants-2009_01
Patent number
US07482340B2

Reaction notes

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