Ammonium Acetate → HCID 178513984, compound

HRID 592036Notes

Reaction equation

HRID 592036 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([N:9]2[CH2:13][CH2:12][CH2:11][CH2:10]2)[S:5][C:6]=1[CH:7]=O.[NH2:14][C:15]1[C:20]([NH2:21])=[C:19]([NH:22][C@@H:23]2[C@@H:28]3[CH2:29][C@@H:25]([CH:26]=[CH:27]3)[C@@H:24]2[C:30]([NH2:32])=[O:31])[C:18]([Br:33])=[CH:17][N:16]=1.C([O-])(=O)C.[NH4+]>>[Br:33][C:18]1[C:19]([NH:22][C@@H:23]2[C@@H:28]3[CH2:29][C@@H:25]([CH:26]=[CH:27]3)[C@@H:24]2[C:30]([NH2:32])=[O:31])=[C:20]2[N:21]=[C:7]([C:6]3[S:5][C:4]([N:9]4[CH2:13][CH2:12][CH2:11][CH2:10]4)=[N:3][C:2]=3[Cl:1])[NH:14][C:15]2=[N:16][CH:17]=1

Participants

4

Reactant 3

HCID 517165Ammonium AcetateHCID 27630664-Chloro-2-(pyrrolidin-1-yl)-1,3-thiazole-5-carbaldehydeHCID 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 178513984HCID 178513984, compoundYield 5.2%

Procedure

In a similar fashion to Compound LXXXVII, 4-Chloro-2-pyrrolidin-1-yl-thiazole-5-carbaldehyde (204.9 mg, 0.9456 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 (290 mg, 0.85 mmol), and Ammonium acetate (131.2 mg, 1.702 mmol) were reacted to produce 23.46 mg (5%) of the title compound. (300 MHz, DMSO-d6) 2.68 (s, 1H), 8.00 (s, 1H), 7.74 (m, 2H), 7.23 (s, 1H), 7.13 (m, 1H), 6.38-6.31 (m, 2H), 5.05 (t, J=17 Hz, 8.5 Hz, 1H), 3.44 m, 4H), 2.87 (s, 1H), 2.73 (s, 1H), 2.58 (d, J=8 Hz, 1H), 2.21 (d, J=8 Hz, 1H), 2.01 (m, 5H). MS=535 (M+H), HPLC: 2.54 min. (G Method)

Sources & evidence

ORD record
ord-a15267b53df142858d8fe13407b42efb
Source dataset
uspto-grants-2016_01
Patent number
US09238656B2

Reaction notes

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