Ammonium Acetate → HCID 178521712, compound

HRID 592041Notes

Reaction equation

HRID 592041 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([N:9]2[CH2:13][CH2:12][CH:11]([OH:14])[CH2:10]2)[S:5][C:6]=1[CH:7]=O.[CH:15]1([NH:18][C:19]([C@@H:21]2[C@H:26]([NH:27][C:28]3[C:33]([Cl:34])=[CH:32][N:31]=[C:30]([NH2:35])[C:29]=3[NH2:36])[C@@H:25]3[CH2:37][C@H:22]2[CH:23]=[CH:24]3)=[O:20])[CH2:17][CH2:16]1.C([O-])(=O)C.[NH4+]>>[CH:15]1([NH:18][C:19]([C@@H:21]2[C@H:26]([NH:27][C:28]3[C:33]([Cl:34])=[CH:32][N:31]=[C:30]4[NH:35][C:7]([C:6]5[S:5][C:4]([N:9]6[CH2:13][CH2:12][C@@H:11]([OH:14])[CH2:10]6)=[N:3][C:2]=5[Cl:1])=[N:36][C:29]=34)[C@@H:25]3[CH2:37][C@H:22]2[CH:23]=[CH:24]3)=[O:20])[CH2:17][CH2:16]1

Participants

4

Reactant 3

HCID 517165Ammonium AcetateHCID 80687886HCID 80687886, compoundHCID 117702036HCID 117702036, compound

Product 1

HCID 178521712HCID 178521712, compoundYield 11.1%

Procedure

In a similar fashion to Compound LXXXVII, 4-Chloro-2-(3-hydroxy-pyrrolidin-1-yl)-thiazole-5-carbaldehyde (174.40 mg, 0.74951 mmol), (1S,2S,3R,4R)-3-(2,3-Diamino-5-chloro-pyridin-4-ylamino)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid cyclopropylamide (200 mg, 0.6 mmol), and Ammonium acetate (92.439 mg, 1.1992 mmol) were reacted to produce 36.26 mg (10%) of the title compound. (300 MHz, DMSO-d6) 12.68 (s, 1H), 8.30 (s, 1H), 7.94 (s, 1H), 6.93 (s, 1H), 6.38-6.30 (m, 2H), 4.99 (t, J=17 Hz, 8.5 Hz, 1H), 3.44 (m, 4H), 2.84 (s, 1H), 2.76 (s, 1H), 2.66 (m, 1H), 2.23 (d, J=8 Hz, 1H), 2.01 (m, 4H), 1.38 (d, J=8 Hz, 1H), 0.63 (m, 2H), 0.37 (m, 2H). MS=546 (M+H), HPLC: 2.35 min. (G Method)

Sources & evidence

ORD record
ord-caf8940a813c45a2a2d034f92b23f679
Source dataset
uspto-grants-2016_01
Patent number
US09238656B2

Reaction notes

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