Ammonium Acetate → HCID 178434059, compound

HRID 591999Notes

Reaction equation

HRID 591999 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][N:22]1[C:26]([N:27]2[CH2:32][CH2:31][O:30][CH2:29][CH2:28]2)=[C:25]([CH:33]=O)[C:24]([CH3:35])=[N:23]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:33]([C:25]3[C:24]([CH3:35])=[N:23][N:22]([CH3:21])[C:26]=3[N:27]3[CH2:28][CH2:29][O:30][CH2:31][CH2:32]3)[NH:1][C:2]2=[N:3][CH:4]=1

Participants

4

Reactant 3

HCID 517165Ammonium AcetateHCID 27764941,3-Dimethyl-5-(morpholin-4-yl)-1H-pyrazole-4-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 178434059HCID 178434059, compoundYield 35%

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), 1,3-Dimethyl-5-morpholin-4-yl-1H-pyrazole-4-carbaldehyde (39.2 mg, 0.187 mmol), and Ammonium acetate (26.2 mg, 0.340 mmol) were reacted to produce 28.80 mg (35%) of the title compound. (300 MHz, DMSO-d6) 12.67 (s, 1H), 7.93 (s, 1H), 7.68 (m, 1H), 7.18 (s, 1H), 6.98 (d, J=8.5 Hz, 1H), 6.31 (d, J=15 Hz, 2H), 5.28 (t, J=17 Hz, 9 Hz, 1H), 3.65 (m, 7H), 3.04 (m, 4H), 2.94 (m, 2H), 2.84 (s, 1H), 2.74 (s, 1H), 2.57 (d, J=9 Hz, 1H), 2.27 (d, J=9 Hz, 1H), 2.18 (s, 3H), 1.40 (d, J=8 Hz, 1H). MS=483 (M+H), HPLC: 1.99 min. (G Method)

Sources & evidence

ORD record
ord-bdf1a9c01dca4657952aaebb093e5019
Source dataset
uspto-grants-2016_01
Patent number
US09238656B2

Reaction notes

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