Ammonium Acetate → HCID 178513980, compound

HRID 592010Notes

Reaction equation

HRID 592010 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[CH:32]=[C:31]([CH:33]=O)[CH:30]=[CH:29][N:28]=2)[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1.C([O-])(=O)C.[NH4+]>>[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:31]3[CH:30]=[CH:29][N:28]=[C:27]([N:21]4[CH2:26][CH2:25][O:24][CH2:23][CH2:22]4)[CH:32]=3)[NH:1][C:2]2=[N:3][CH:4]=1

Participants

4

Reactant 3

HCID 517165Ammonium AcetateHCID 75375632-MorpholinoisonicotinaldehydeHCID 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 178513980HCID 178513980, compoundYield 86.5%

Procedure

In a similar fashion to Compound CXXV, (1S,2S,3R,4R)-3-(2,3-Diamino-5-bromo-pyridin-4-ylamino)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid amide (57.57 mg, 0.1702 mmol), 2-Morpholin-4-yl-pyridine-4-carbaldehyde (36.0 mg, 0.187 mmol), and Ammonium acetate (26.2 mg, 0.340 mmol) were reacted to produce 75.1 mg (86%) of the title compound. (300 MHz, DMSO-d6) 13.47 (s, 1H), 8.28 (d, J=5 Hz, 1H), 8.08 (s, 1H), 7.76 (s, 1H), 7.52 s, 1H), 7.36 (d, J=5 Hz, 1H), 7.33 (d, J=8 Hz, 1H), 7.24 (s, 1H), 6.39 (s, 2H), 5.20 (t, J=17 Hz, 8.5 Hz, 1H), 3.75 (m, 4H), 3.54 (s, 4H), 2.90 (s, 1H), 2.79 (s, 1H), 2.62 (d, J=8 Hz, 1H), 2.24 (d, J=8 Hz, 1H), 1.38 (d, J=8 Hz, 1H). MS=512 (M+H), HPLC: 1.78 min. (G Method)

Sources & evidence

ORD record
ord-6e7262378b4d43bd954144022169426b
Source dataset
uspto-grants-2016_01
Patent number
US09238656B2

Reaction notes

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