Ammonium Acetate → HCID 178483049, compound

HRID 592027Notes

Reaction equation

HRID 592027 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[N:23]=[C:24]([N:29]([CH3:31])[CH3:30])[S:25][C:26]=1[CH:27]=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:27]([C:26]3[S:25][C:24]([N:29]([CH3:31])[CH3:30])=[N:23][C:22]=3[Cl:21])[NH:1][C:2]2=[N:3][CH:4]=1

Participants

4

Reactant 3

HCID 517165Ammonium AcetateHCID 91183764-chloro-2-(dimethylamino)-1,3-thiazole-5-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 178483049HCID 178483049, compoundYield 24.5%

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 (75.00 mg, 0.2553 mmol), 4-Chloro-2-dimethylamino-thiazole-5-carbaldehyde (53.5 mg, 0.281 mmol), and Ammonium acetate (39.4 mg, 0.511 mmol) were reacted to produce 29.03 mg (24%) of the title compound. (300 MHz, DMSO-d6) 7.93 (s, 1H), 7.76 (s, 1H), 7.23 (m, 2H), 6.38-6.31 (m, 2H), 4.99 (t, J=17 Hz, 8.5 Hz, 1H), 3.11 (s, 6H), 2.87 (s, 4H), 2.75 (s, 1H), 2.58 (d, J=8 Hz, 1H), 2.19 (d, J=8 Hz, 1H), 1.36 (d, J=8 Hz, 1H). MS=464 (M+H), HPLC: 2.37 min. (G Method)

Sources & evidence

ORD record
ord-49b8d09a3183403da476b92733b0ec5a
Source dataset
uspto-grants-2016_01
Patent number
US09238656B2

Reaction notes

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