Ammonium Acetate → HCID 117701743, compound

HRID 592038Notes

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]([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[N:35]=[C:7]([C:6]4[S:5][C:4]([N:9]5[CH2:13][CH2:12][C@@H:11]([OH:14])[CH2:10]5)=[N:3][C:2]=4[Cl:1])[NH: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 80687886HCID 80687886, compound

HCID 117701981HCID 117701981, compound

Product 1

HCID 117701743HCID 117701743, compoundYield 7%

Procedure

In a similar fashion to Compound LXXXVII, 4-Chloro-2-(3-hydroxy-pyrrolidin-1-yl)-thiazole-5-carbaldehyde (180.77 mg, 0.77687 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 (208.72 mg, 0.62149 mmol), and Ammonium acetate (95.813 mg, 1.2430 mmol) were reacted to produce 23.87 mg (7%) of the title compound. (300 MHz, DMSO-d6) 12.60 (s, 1H), 8.10 (d, J=7 Hz, 1H), 7.92 (s, 1H), 6.38-6.31 (m, 2H), 5.16 (m, 1H), 5.02 (T, J=17 Hz, 9 Hz, 1H), 4.44 (s, 1H), 3.88 (m, 1H), 3.54 (m, 3H), 2.83 (s, 1H), 2.76 (s, 1H), 2.55 (d, J=8 Hz, 1H), 2.24 (d, J=8 Hz, 1H), 2.10 (m, 1H), 1.96 (m, 1H), 1.38 (d, J=8 Hz, 1H), 1.06 (d, J=7 Hz, 3H), 0.99 (d, J=7 Hz, 3H). MS=548 (M+H), HPLC: 2.52 min. (G Method)

Sources & evidence

ORD record: ord-6239b39f4f5e490fa8041af78f5167ac
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09238656B2

Reaction notes

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