Ammonium Acetate → HCID 178428038, compound

HRID 592006Notes

Reaction equation

HRID 592006 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]([Br: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+]>>[Br: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 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 178428038HCID 178428038, compoundYield 32%

Procedure

In a similar fashion to compound CXXV, (1S,2S,3R,4R)-3-(2,3-Diamino-5-bromo-pyridin-4-ylamino)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid amide (100.00 mg, 0.29568 mmol), 2-Methyl-4-morpholin-4-yl-benzaldehyde (66.8 mg, 0.325 mmol), and Ammonium acetate (45.6 mg, 0.591 mmol) were reacted to yield 48.7 mg (32%) of the title compound. (300 MHz, DMSO-d6) 12.85 (s, 1H), 8.00 (s, 1H), 7.71 (m, 2H), 7.19 (s, 1H), 6.92 (m, 2H), 6.34 (s, 1H), 6.26 (s, 1H), 5.30 (t, J=17 Hz, 8. Hz, 1H), 3.75 (s, 4H), 3.22 (s, 4H), 2.85 (s, 1H), 2.73 (s, 1H), 2.65 (s, 3H), 2.59 (d, J=8 Hz, 1H) 2.24 (d, J=8 Hz, 1H), 1.38 (d, J=8 Hz, 1H). MS=525 (M+H), HPLC: 2.43 min. (G Method)

Sources & evidence

ORD record
ord-0d04961b0a164681852278c7daefb89f
Source dataset
uspto-grants-2016_01
Patent number
US09238656B2

Reaction notes

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