Ammonium Acetate → HCID 178521711, compound

HRID 592040Notes

Reaction equation

[CH:1]1([NH:4][C:5]([C@@H:7]2[C@H:12]([NH:13][C:14]3[C:19]([Cl:20])=[CH:18][N:17]=[C:16]([NH2:21])[C:15]=3[NH2:22])[C@@H:11]3[CH2:23][C@H:8]2[CH:9]=[CH:10]3)=[O:6])[CH2:3][CH2:2]1.[Cl:24][C:25]1[N:26]=[C:27]([N:32]2[CH2:36][CH2:35][CH2:34][CH2:33]2)[S:28][C:29]=1[CH:30]=O.C([O-])(=O)C.[NH4+]>>[CH:1]1([NH:4][C:5]([C@@H:7]2[C@H:12]([NH:13][C:14]3[C:19]([Cl:20])=[CH:18][N:17]=[C:16]4[NH:21][C:30]([C:29]5[S:28][C:27]([N:32]6[CH2:36][CH2:35][CH2:34][CH2:33]6)=[N:26][C:25]=5[Cl:24])=[N:22][C:15]=34)[C@@H:11]3[CH2:23][C@H:8]2[CH:9]=[CH:10]3)=[O:6])[CH2:3][CH2:2]1

Participants

Reactant 3

HCID 517165Ammonium Acetate

HCID 27630664-Chloro-2-(pyrrolidin-1-yl)-1,3-thiazole-5-carbaldehyde

HCID 117702036HCID 117702036, compound

Product 1

HCID 178521711HCID 178521711, compoundYield 8.2%

Procedure

In a similar fashion to Compound LXXXVII, (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), 4-Chloro-2-pyrrolidin-1-yl-thiazole-5-carbaldehyde (162.28 mg, 0.74892 mmol), and Ammonium acetate (92.439 mg, 1.1992 mmol) were reacted to produce 26.23 mg (8%) of the title compound. (300 MHz, DMSO-d6) 12.68 (s, 1H), 8.31 (s, 1H), 7.94 (s, 1H), 6.93 (s, 1H), 6.38-6.31 (m, 2H), 4.99 (t, J=17 Hz, 8.5 Hz, 1H), 3.44 (m, 4H), 2.84 (s, 1H), 2.75 (s, 1H), 2.65 (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=530 (M+H), HPLC: 2.90 min. (G Method)

Sources & evidence

ORD record: ord-1b13cb393912487b9d1059dc3b1b1008
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09238656B2

Reaction notes

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