HCID 89725856, compound → HCID 178492019, compound

HRID 591959Notes

Reaction equation

HRID 591959 reaction equation
[NH2:1][C:2]1[C:7]([NH2:8])=[C:6]([NH:9][C@@H:10]2[C@@H:15]3[CH2:16][C@@H:12]([CH:13]=[CH:14]3)[C@@H:11]2[C:17]([NH2:19])=[O:18])[C:5]([Cl:20])=[CH:4][N:3]=1.[N:21]([C:24]1[CH:36]=[CH:35][C:27]([CH2:28][N:29]2[CH2:34][CH2:33][O:32][CH2:31][CH2:30]2)=[CH:26][C:25]=1[O:37][CH3:38])=[C:22]=S>>[Cl:20][C:5]1[C:6]([NH:9][C@@H:10]2[C@@H:15]3[CH2:16][C@@H:12]([CH:13]=[CH:14]3)[C@@H:11]2[C:17]([NH2:19])=[O:18])=[C:7]2[N:8]=[C:22]([NH:21][C:24]3[CH:36]=[CH:35][C:27]([CH2:28][N:29]4[CH2:34][CH2:33][O:32][CH2:31][CH2:30]4)=[CH:26][C:25]=3[O:37][CH3:38])[NH:1][C:2]2=[N:3][CH:4]=1

Participants

3

Reactant 2

HCID 89725856HCID 89725856, compoundHCID 117701912(1S,2S,3R,4R)-3-(2,3-Diamino-5-chloro-pyridin-4-ylamino)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid amide

Product 1

HCID 178492019HCID 178492019, compoundYield 11%

Procedure

In a similar fashion as for the synthesis of Compound LXVII, (1S,2S,3R,4R)-3-(2,3-Diamino-5-chloro-pyridin-4-ylamino)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid amide was reacted with 4-(4-isothiocyanato-3-methoxybenzyl)-morpholine to afford the title compound as a tan solid (11%). 1H NMR (d-6 DMSO): 10.0 (br m, 1H), 8.78 (m, 1H), 8.62 (m, 1H), 7.86 (m, 2H), 7.36 (m, 1H), 7.25 (m, 1H), 7.10 (m, 1H), 6.43 (m, 2H), 5.08 (m, 1H), 4.34 (m, 2H), 3.98 (s, 3H), 3.29 (m, 4H), 3.12 (m, 4H), 2.92 (s, 1H), 2.86 (s, 1H), 2.62 (m, 1H), 2.21 (m, 1H), 1.69 (m, 1H), 1.44 (m, 1H). MS: 524.02 (M+H). HPLC retention time: 1.74 minutes (G Method).

Sources & evidence

ORD record
ord-463109368dc04f8695afb71f2b13333c
Source dataset
uspto-grants-2016_01
Patent number
US09238656B2

Reaction notes

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