2-Morpholinonicotinaldehyde → HCID 178513979, compound

HRID 591981Notes

Reaction equation

HRID 591981 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[C:32]([CH:33]=O)=[CH:31][CH:30]=[CH:29][N: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:32]3[C:27]([N:21]4[CH2:22][CH2:23][O:24][CH2:25][CH2:26]4)=[N:28][CH:29]=[CH:30][CH:31]=3)[NH:1][C:2]2=[N:3][CH:4]=1

Participants

3

Reactant 2

HCID 27765702-MorpholinonicotinaldehydeHCID 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 178513979HCID 178513979, compoundYield 42.4%

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 2-Morpholin-4-yl-pyridine-3-carbaldehyde (31.2 mg, 0.163 mmol) were reacted to produce 32 mg (42%) of the title compound. mp: 150° C., 1H NMR (300 MHz, DMSO-d6): 12.95 (s, 1H), 8.33 (d, J=5 Hz, 1H), 8.04 (s, 1H), 7.98 (d, J=8 Hz, 1H), 7.73 (s, 1H), 7.19 (s, 1H), 7.09 (m, 1H), 6.34 (s, 1H), 6.32 (s, 1H), 5.21 (t, J=8 Hz, 1H), 3.64 (s, 4H), 3.29 (s, 1H), 3.06 (m, 4H), 2.87 (s, 1H), 2.78 (s, 1H), 2.59 (d, J=8 Hz, 1H), 2.26 (d, J=8 Hz, 1H), 1.39 (d, J=8 Hz, 1H). MS: 510, 512 (M+H), HPLC: 2.02 min (G method).

Sources & evidence

ORD record
ord-8b9de8f1956f430ea0311f3049e6f6ab
Source dataset
uspto-grants-2016_01
Patent number
US09238656B2

Reaction notes

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