Ammonium Acetate → HCID 178514002, compound

HRID 592011Notes

Reaction equation

HRID 592011 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.[Cl:21][C:22]1[CH:23]=[C:24]([CH:27]=[CH:28][C:29]=1[N:30]1[CH2:35][CH2:34][O:33][CH2:32][CH2:31]1)[CH:25]=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:25]([C:24]3[CH:27]=[CH:28][C:29]([N:30]4[CH2:35][CH2:34][O:33][CH2:32][CH2:31]4)=[C:22]([Cl:21])[CH:23]=3)[NH:1][C:2]2=[N:3][CH:4]=1

Participants

4

Reactant 3

HCID 517165Ammonium AcetateHCID 71486043-Chloro-4-morpholinobenzaldehydeHCID 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 178514002HCID 178514002, compoundYield 37%

Procedure

In a similar fashion to Compound CXXV, (1S,2S,3R,4R)-3-(2,3-Diamino-5-chloro-pyridin-4-ylamino)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid amide (100.00 mg, 0.34042 mmol), 3-Chloro-4-morpholin-4-yl-benzaldehyde (84.5 mg, 0.374 mmol), and Ammonium acetate (52.5 mg, 0.681 mmol) were reacted to produce 62.66 mg (37%) of the title compound. (300 MHz, DMSO-d6) 13.35 (s, 1H), 8.28 (d, J=5 Hz, 1H), 8.01 (s, 1H), 7.78 (s, 1H), 7.52 (m, 1H), 7.38 (m, 2H), 7.25 (s, 1H), 6.38 (m, 2H), 5.14 (t, J=16 Hz, 8 Hz, 1H), 3.76 (m, 4H), 3.54 (s, 4H), 2.91 (s, 1H), 2.81 (s, 1H), 2.63 (d, J=8 Hz, 1H), 2.22 (d, J=9 Hz, 1H), 1.39 (d, J=9 Hz, 1H). MS=466 (M-Cl+), HPLC: 1.76 min. (G Method)

Sources & evidence

ORD record
ord-b564007705b14b1db42bff901a407c03
Source dataset
uspto-grants-2016_01
Patent number
US09238656B2

Reaction notes

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