Ammonium Acetate → HCID 178513970, compound

HRID 592012Notes

Reaction equation

HRID 592012 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.[F:21][C:22]([F:32])([F:31])[C:23]1[N:28]=[CH:27][C:26]([CH:29]=O)=[CH:25][CH:24]=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:29]([C:26]3[CH:27]=[N:28][C:23]([C:22]([F:32])([F:21])[F:31])=[CH:24][CH:25]=3)[NH:1][C:2]2=[N:3][CH:4]=1

Participants

4

Reactant 3

HCID 517165Ammonium AcetateHCID 27777626-(Trifluoromethyl)pyridine-3-carboxaldehydeHCID 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 178513970HCID 178513970, compoundYield 5.5%

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 (75.00 mg, 0.2218 mmol), 6-Trifluoromethyl-pyridine-3-carbaldehyde (42.7 mg, 0.244 mmol), and Ammonium acetate (34.2 mg, 0.444 mmol) were reacted to produce 5.98 mg (5%) of the title compound. (300 MHz, DMSO-d6) 9.45 (s, 1H), 8.69 (d, J=9 Hz, 1H), 8.09 (m, 2H), 7.76 (s, 1H), 7.22 (s, 2H), 6.44 (m, 1H), 6.37 (m, 1H), 5.24 (t, J=17 Hz, 8 Hz, 1H), 2.89 (s, 1H), 2.79 (s, 1H), 2.66 (d, J=9 Hz, 1H), 2.63 (d, J=9 Hz, 1H), 2.25 (d, J=8 Hz, 1H), 1.39 (d, J=8 Hz, 1H). MS=493 (M+H), HPLC: 2.66 min. (G Method)

Sources & evidence

ORD record
ord-cc4d6053b7694410a4473725b4b255c2
Source dataset
uspto-grants-2016_01
Patent number
US09238656B2

Reaction notes

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