Ammonium Acetate → HCID 178494113, compound

HRID 592000Notes

Reaction equation

HRID 592000 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]([Cl:20])=[CH:4][N:3]=1.[CH3:21][O:22][C:23]1[C:28]([CH:29]=O)=[CH:27][CH:26]=[CH:25][N:24]=1.C([O-])(=O)C.[NH4+]>>[Cl: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:29]([C:28]3[C:23]([O:22][CH3:21])=[N:24][CH:25]=[CH:26][CH:27]=3)[NH:1][C:2]2=[N:3][CH:4]=1

Participants

4

Reactant 3

HCID 517165Ammonium AcetateHCID 125333912-Methoxypyridine-3-carbaldehydeHCID 117701912(1S,2S,3R,4R)-3-(2,3-Diamino-5-chloro-pyridin-4-ylamino)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid amide

Product 1

HCID 178494113HCID 178494113, compoundYield 12.2%

Procedure

In a similar fashion to Compound LXXXVII, (1S,2S,3R,4R)-3-(2,3-Diamino-5-chloro-pyridin-4-ylamino)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid amide (50.00 mg, 0.1702 mmol), 2-Methoxy-pyridine-3-carbaldehyde (25.7 mg, 0.187 mmol), and Ammonium acetate (26.2 mg, 0.340 mmol) were reacted to produce 8.5 mg (12%) of the title compound. (300 MHz, DMSO-d6) 12.61 (s, 1H), 8.46 (d, J=7.5 Hz, 1H), 8.31 (s, 1H), 7.99 (s, 1H), 7.76 (s, 1H), 7.21 (m, 3H), 6.38 (d, J=19 Hz, 2H), 5.17 (t, J=17 Hz, J=9 Hz, 1H), 4.05 (s, 3H), 2.89 (s, 1H), 2.80 (s, 1H), 2.61 (d, J=9 Hz, 1H), 2.24 (d, J=9 Hz, 1H), 1.39 (d, J=9 Hz, 1H). MS=411 (M+H), HPLC: 2.33 min. (G Method)

Sources & evidence

ORD record
ord-8c48986ba25547dab3067af34bacf780
Source dataset
uspto-grants-2016_01
Patent number
US09238656B2

Reaction notes

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