Ammonium Acetate → HCID 178513985, compound

HRID 592039Notes

Reaction equation

HRID 592039 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([N:9]2[CH2:13][CH2:12][CH:11]([OH:14])[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]([Br:34])=[CH:18][N:17]=1.C([O-])(=O)C.[NH4+]>>[Br: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[CH2:13][CH2:12][C@@H:11]([OH:14])[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 80687886HCID 80687886, compoundHCID 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 178513985HCID 178513985, compoundYield 4%

Procedure

In a similar fashion to Compound LXXXVII, 4-Chloro-2-(3-hydroxy-pyrrolidin-1-yl)-thiazole-5-carbaldehyde (180.77 mg, 0.77687 mmol), (1S,2S,3R,4R)-3-(2,3-Diamino-5-bromo-pyridin-4-ylamino)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid amide (210.19 mg, 0.62149 mmol), and Ammonium acetate (95.813 mg, 1.2430 mmol) were reacted to produce 13.82 mg (4%) of the title compound. (300 MHz, DMSO-d6) 12.68 (s, 1H), 8.01 (s, 1H), 7.73 (s, 1H), 7.23 (s, 1H), 7.14 (s, 1H), 6.38-6.31 (m, 2H), 5.15 (s, 1H), 5.05 (t, J=17 Hz, 8.5 Hz, 1H), 4.44 (s, 1H), 3.54 (m, 3H), 2.87 (s, 1H), 2.73 (s, 1H), 2.59 (d, J=8 Hz, 1H), 2.21 (d, J=8 Hz, 1H), 2.10 (m, 1H), 1.96 (m, 1H), 1.38 (d, J=8 Hz, 1H). MS=553 (M+H), HPLC: 2.07 min. (G Method)

Sources & evidence

ORD record
ord-deb9b2e9387c4ae1baf1784e677046a4
Source dataset
uspto-grants-2016_01
Patent number
US09238656B2

Reaction notes

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