Ammonium Acetate → HCID 178484585, compound

HRID 592032Notes

Reaction equation

HRID 592032 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.[CH3:15][N:16]([CH3:36])[C:17]([C@@H:19]1[C@H:24]([NH:25][C:26]2[C:31]([Cl:32])=[CH:30][N:29]=[C:28]([NH2:33])[C:27]=2[NH2:34])[C@@H:23]2[CH2:35][C@H:20]1[CH:21]=[CH:22]2)=[O:18].C([O-])(=O)C.[NH4+]>>[CH3:15][N:16]([CH3:36])[C:17]([C@@H:19]1[C@H:24]([NH:25][C:26]2[C:31]([Cl:32])=[CH:30][N:29]=[C:28]3[NH:33][C:7]([C:6]4[S:5][C:4]([N:9]5[CH2:14][CH2:13][O:12][CH2:11][CH2:10]5)=[N:3][C:2]=4[Cl:1])=[N:34][C:27]=23)[C@@H:23]2[CH2:35][C@H:20]1[CH:21]=[CH:22]2)=[O:18]

Participants

4

Reactant 3

HCID 517165Ammonium AcetateHCID 27630654-Chloro-2-(morpholin-4-yl)-1,3-thiazole-5-carbaldehydeHCID 117701995HCID 117701995, compound

Product 1

HCID 178484585HCID 178484585, compoundYield 16%

Procedure

In a similar fashion to Compound LXXXVII, 4-Chloro-2-morpholin-4-yl-thiazole-5-carbaldehyde (75.00 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 24.34 mg (16%) of the title compound. (300 MHz, DMSO-d6) 12.80 (s, 1H), 7.96 (s, 1H), 6.42-6.32 (m, 2H), 5.11 (t, J=17 Hz, 8.5 Hz, 1H), 3.73 (m, 4H), 3.48 (m, 4H), 3.01 (d, J=9 Hz, 1H), 2.94 (s, 3H), 2.86 (m, 4H), 2.82 (s, 1H), 2.11 (d, J=8 Hz, 1H), 1.42 (d, J=8 Hz, 1H). MS=533 (M+H), HPLC: 2.73 min. (G Method)

Sources & evidence

ORD record
ord-52817d260351445aaace11b588baade8
Source dataset
uspto-grants-2016_01
Patent number
US09238656B2

Reaction notes

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