Ammonium Acetate → HCID 178484583, compound

HRID 592034Notes

Reaction equation

HRID 592034 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.[CH3:14][N:15]([CH3:35])[C:16]([C@@H:18]1[C@H:23]([NH:24][C:25]2[C:30]([Cl:31])=[CH:29][N:28]=[C:27]([NH2:32])[C:26]=2[NH2:33])[C@@H:22]2[CH2:34][C@H:19]1[CH:20]=[CH:21]2)=[O:17].C([O-])(=O)C.[NH4+]>>[CH3:14][N:15]([CH3:35])[C:16]([C@@H:18]1[C@H:23]([NH:24][C:25]2[C:30]([Cl:31])=[CH:29][N:28]=[C:27]3[NH:32][C:7]([C:6]4[S:5][C:4]([N:9]5[CH2:13][CH2:12][CH2:11][CH2:10]5)=[N:3][C:2]=4[Cl:1])=[N:33][C:26]=23)[C@@H:22]2[CH2:34][C@H:19]1[CH:20]=[CH:21]2)=[O:17]

Participants

4

Reactant 3

HCID 517165Ammonium AcetateHCID 27630664-Chloro-2-(pyrrolidin-1-yl)-1,3-thiazole-5-carbaldehydeHCID 117701995HCID 117701995, compound

Product 1

HCID 178484583HCID 178484583, compoundYield 5%

Procedure

In a similar fashion to Compound LXXXVII 4-Chloro-2-pyrrolidin-1-yl-thiazole-5-carbaldehyde (69.84 mg, 0.3223 mmol), (1S,2S,3R,4R)-3-(2,3-Diamino-5-chloro-pyridin-4-ylamino)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid dimethylamide (93.35 mg, 0.2901 mmol and Ammonium acetate (44.72 mg, 0.5802 mmol) were reacted to produce 7.35 mg (5%) of the title compound. (300 MHz, DMSO-d6) 13.50 (s, 1H), 7.94 (s, 1H), 6.67 (s, 1H), 6.38 (m, 2H), 5.12 (t, J=17 Hz, 8.5 Hz, 1H), 3.44 (m, 4H), 3.02 (d, J=9 Hz, 1H), 2.94 (s, 3H), 2.86 (m, 4H), 2.82 (s, 1H), 2.11 (d, J=8 Hz, 1H), 2.01 (m, 4H), 1.42 (d, J=8 Hz, 1H). MS=517 (M+H), HPLC: 2.96 min. (G Method)

Sources & evidence

ORD record
ord-4bf7d628654f4a3e89f414bacb9d4ef0
Source dataset
uspto-grants-2016_01
Patent number
US09238656B2

Reaction notes

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