Ammonium Acetate → HCID 178457876, compound

HRID 592033Notes

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.[CH:15]([NH:18][C:19]([C@@H:21]1[C@H:26]([NH:27][C:28]2[C:33]([Cl:34])=[CH:32][N:31]=[C:30]([NH2:35])[C:29]=2[NH2:36])[C@@H:25]2[CH2:37][C@H:22]1[CH:23]=[CH:24]2)=[O:20])([CH3:17])[CH3:16].C([O-])(=O)C.[NH4+]>>[CH:15]([NH:18][C:19]([C@@H:21]1[C@H:26]([NH:27][C:28]2[C:33]([Cl:34])=[CH:32][N:31]=[C:30]3[NH:35][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:36][C:29]=23)[C@@H:25]2[CH2:37][C@H:22]1[CH:23]=[CH:24]2)=[O:20])([CH3:17])[CH3:16]

Participants

Reactant 3

HCID 517165Ammonium Acetate

HCID 27630654-Chloro-2-(morpholin-4-yl)-1,3-thiazole-5-carbaldehyde

HCID 117701981HCID 117701981, compound

Product 1

HCID 178457876HCID 178457876, compoundYield 9%

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 isopropylamide (97.42 mg, 0.2901 mmol), and Ammonium acetate (44.72 mg, 0.5802 mmol were reacted to produce 14.26 mg (9%) of the title compound. (300 MHz, DMSO-d6) 12.78 (s, 1H), 8.11 (d, J=7.5 Hz, 1H), 7.94 (s, 1H), 6.95 (s, 1H), 6.39-6.29 (m, 2H), 4.98 (t, J=17 Hz, 8.5 Hz, 1H), 3.88 (m, 1H), 3.73 (m, 4H), 3.49 (m, 4H), 2.83 (s, 1H), 2.83 (s, 1H), 2.76 (s, 1H), 2.54 (d, J=8 Hz, 1H), 2.54 (d, J=8 Hz, 1H), 2.25 (d, J=8 Hz, 1H), 1.07 (d, J=6.5 Hz, 3H, 1.00 (d, J=6.5 Hz, 3H). MS=547 (M+H), HPLC: 2.92 min. (G Method)

Sources & evidence

ORD record: ord-3d7c966c7e6a4a66abd4680efbe55f21
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09238656B2

Reaction notes

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