Ammonium Acetate → HCID 178514007, compound

HRID 592031Notes

Reaction equation

HRID 592031 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)[S:5][C:6]=1[CH:7]=O.[NH2:15][C:16]1[C:21]([NH2:22])=[C:20]([NH:23][C@@H:24]2[C@@H:29]3[CH2:30][C@@H:26]([CH:27]=[CH:28]3)[C@@H:25]2[C:31]([NH2:33])=[O:32])[C:19]([Cl:34])=[CH:18][N:17]=1.C([O-])(=O)C.[NH4+]>>[Cl:34][C:19]1[C:20]([NH:23][C@@H:24]2[C@@H:29]3[CH2:30][C@@H:26]([CH:27]=[CH:28]3)[C@@H:25]2[C:31]([NH2:33])=[O:32])=[C:21]2[N:22]=[C:7]([C:6]3[S:5][C:4]([N:9]4[CH2:14][CH2:13][O:12][CH2:11][CH2:10]4)=[N:3][C:2]=3[Cl:1])[NH:15][C:16]2=[N:17][CH:18]=1

Participants

4

Reactant 3

HCID 517165Ammonium AcetateHCID 27630654-Chloro-2-(morpholin-4-yl)-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 178514007HCID 178514007, compoundYield 11%

Procedure

In a similar fashion to Compound LXXXVII, 4-Chloro-2-morpholin-4-yl-thiazole-5-carbaldehyde (65 mg, 0.28 mmol), (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 mg, 0.26 mmol), and Ammonium acetate (98 mg, 1.3 mmol) were reacted to produce 13.87 mg (11%) of the title compound. (300 MHz, DMSO-d6) 12.79 (s, 1H), 7.95 (s, 1H), 7.77 (s, 2H), 7.25 (s, 2H), 6.40-6.30 (m, 2H), 4.98 (t, J=17 Hz, 8.5 Hz, 1H), 3.72 (m, 4H), 3.27 (m, 4H), 3.48 (m, 4H), 2.87 (s, 1H), 2.75 (s, 1H), 2.57 (d, J=8 Hz, 1H), 2.19 (d, J=8 Hz, 1H), 1.36 (d, J=8 Hz, 1H). MS=507 (M+H), HPLC: 2.35 min. (G Method)

Sources & evidence

ORD record
ord-4b43f853ca014c2a98c72a8ec23156fc
Source dataset
uspto-grants-2016_01
Patent number
US09238656B2

Reaction notes

Loading…