HCID 89725999, compound → HCID 178487549, compound

HRID 591994Notes

Reaction equation

HRID 591994 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.[CH3:21][O:22][C:23]1[CH:30]=[C:29]([CH:31]2[CH2:36][CH2:35][N:34]([CH3:37])[CH2:33][CH2:32]2)[CH:28]=[CH:27][C:24]=1[CH:25]=O>>[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:25]([C:24]3[CH:27]=[CH:28][C:29]([CH:31]4[CH2:32][CH2:33][N:34]([CH3:37])[CH2:35][CH2:36]4)=[CH:30][C:23]=3[O:22][CH3:21])[NH:1][C:2]2=[N:3][CH:4]=1

Participants

3

Reactant 2

HCID 89725999HCID 89725999, 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 178487549HCID 178487549, compoundYield 49%

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 amide (125 mg, 0.427 mmol) and 2-Methoxy-4-(1-methyl-piperidin-4-yl)-benzaldehyde (109.5 mg, 0.469 mmol) were reacted to produce 106 mg (49%) of the title compound. mp: 232-235° C., 1H NMR (300 MHz, CDCl3): 10.67 (s, 1H), 8.33 (d, J=8 Hz, 1H), 8.04 (s, 1H), 7.04 (d, J=8 Hz, 1H), 6.96 (s, 1H), 6.42 (m, 1H), 6.38 (m, 1H), 6.35 (m, 1H), 5.48 (d, J=8 Hz, 1H), 5.18 (t, J=8 Hz, 1H), 5.05 (s, 1H), 4.06 (s, 3H), 3.19 (s, 1H), 3.03 (d, J=10 Hz, 2H), 2.91 (m, 2H), 2.57 (m, 1H), 2.37 (s, 3H), 2.34 (s, 1H), 2.10 (m, 2H), 1.89 (m, 4H), 1.76 (d, J=8 Hz, 1H), 1.27 (s, 2H). MS: 507 (M+H), HPLC: 1.86 min (G method)

Sources & evidence

ORD record
ord-2a1181d367f6426582de4e111d5cc040
Source dataset
uspto-grants-2016_01
Patent number
US09238656B2

Reaction notes

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