6-(Morpholin-4-yl)pyridine-3-carbaldehyde → HCID 178513977, compound

HRID 591991

Reaction equation

HRID 591991 reaction equation
[NH2:1][C:2]1[C:7]([NH2:8])=[C:6]([NH:9][C@@H:10]2[C@@H:15]3[CH2:16][C@@H:12]([CH:13]=[CH:14]3)[C@@H:11]2[C:17]([NH2:19])=[O:18])[C:5]([Br:20])=[CH:4][N:3]=1.[N:21]1([C:27]2[N:32]=[CH:31][C:30]([CH:33]=O)=[CH:29][CH:28]=2)[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1>>[Br:20][C:5]1[C:6]([NH:9][C@@H:10]2[C@@H:15]3[CH2:16][C@@H:12]([CH:13]=[CH:14]3)[C@@H:11]2[C:17]([NH2:19])=[O:18])=[C:7]2[N:8]=[C:33]([C:30]3[CH:31]=[N:32][C:27]([N:21]4[CH2:26][CH2:25][O:24][CH2:23][CH2:22]4)=[CH:28][CH:29]=3)[NH:1][C:2]2=[N:3][CH:4]=1

Participants

3

Reactant 2

HCID 27764636-(Morpholin-4-yl)pyridine-3-carbaldehydeHCID 117701905(1S,2S,3R,4R)-3-(2,3-Diamino-5-bromo-pyridin-4-ylamino)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid amide

Product 1

HCID 178513977HCID 178513977, compoundYield 74.1%

Procedure

In a similar fashion to Compound LXXXVII, (1S,2S,3R,4R)-3-(2,3-Diamino-5-bromo-pyridin-4-ylamino)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid amide (50 mg, 0.148 mmol) and 6-Morpholin-4-yl-pyridine-3-carbaldehyde (31.2 mg, 0.163 mmol) were reacted to produce 56 mg (74%) of the title compound. mp: 288-290° C., 1H NMR (300 MHz, DMSO-d6): 13.14 (s, 1H), 8.87 (s, 1H), 8.21 (d, J=8 Hz, 2H), 7.98 (s, 1H), 7.74 (s, 1H), 7.20 (s, 1H), 7.02 (m, 2H), 6.36 (s, 2H), 5.25 (t, J=8 Hz, 1H), 3.72 (br s, 4H), 3.57 (br s, 4H), 3.29 (s, 1H), 2.88 (s, 1H), 2.75 (s, 1H), 2.61 (d, J=7 Hz, 1H), 2.25 (d, J=8 Hz, 1H), 1.38 (d, J=8 Hz, 1H). MS: 510, 512 (M+H), HPLC: 1.96 min (G method).

Sources & evidence

ORD record
ord-7ca9c026912b4fbc8e5c0df4d8e97138
Source dataset
uspto-grants-2016_01
Patent number
US09238656B2

Linked notes

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