Ammonium Acetate → HCID 178428039, compound

HRID 591998Notes

Reaction equation

HRID 591998 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][C:22]1[CH:29]=[C:28]([N:30]2[CH2:35][CH2:34][O:33][CH2:32][CH2:31]2)[CH:27]=[CH:26][C:23]=1[CH:24]=O.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:24]([C:23]3[CH:26]=[CH:27][C:28]([N:30]4[CH2:35][CH2:34][O:33][CH2:32][CH2:31]4)=[CH:29][C:22]=3[CH3:21])[NH:1][C:2]2=[N:3][CH:4]=1

Participants

4

Reactant 3

HCID 517165Ammonium AcetateHCID 31525222-Methyl-4-morpholin-4-yl-benzaldehydeHCID 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 178428039HCID 178428039, 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), 2-Methyl-4-morpholin-4-yl-benzaldehyde (38.4 mg, 0.187 mmol), and Ammonium acetate (26.2 mg, 0.340 mmol) were reacted to produce 28.37 mg (35%) of the title compound. (300 MHz, DMSO-d6) 12.83 (s, 1H), 7.91 (s, 1H), 7.72 (m, 2H), 7.21 (s, 1H), 7.00 (d, J=9 Hz, 1H), 6.90 (s, 2H), 6.33 (s, 1H), 6.26 (s, 1H), 5.18 (t, J=17 Hz, 9 Hz, 1H), 3.75 (s, 4H), 3.22 (s, 4H), 2.86 (s, 1H), 2.75 (s, 1H), 2.59 (d, J=8 Hz, 1H), 2.25 (d, J=8 Hz, 1H), 1.39 (d, J=8 Hz). MS=479 (M+H), HPLC: 2.42 min. (G Method)

Sources & evidence

ORD record
ord-33c0ae30f75c428f92e7e4701be3dd77
Source dataset
uspto-grants-2016_01
Patent number
US09238656B2

Reaction notes

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