HCID 83896541, compound → HCID 178493035, compound

HRID 591952Notes

Reaction equation

HRID 591952 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[C:30]([CH2:31][N:32]2[CH2:37][CH2:36][O:35][CH2:34][CH2:33]2)=[CH:29][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][CH:29]=[C:30]([CH2:31][N:32]4[CH2:37][CH2:36][O:35][CH2:34][CH2:33]4)[C:23]=3[O:22][CH3:21])[NH:1][C:2]2=[N:3][CH:4]=1

Participants

3

Reactant 2

HCID 83896541HCID 83896541, 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 178493035HCID 178493035, compoundYield 70%

Procedure

In a similar fashion as for the synthesis of III, (1S,2S,3R,4R)-3-(2,3-Diamino-5-chloro-pyridin-4-ylamino)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid amide and 2-methoxy-3-morpholin-4-ylmethylbenzaldehyde were reacted to produce the title compound (70%). Mp. 133-7° C. 1H NMR (d-chloroform): 12.03 (br s, 1H), 8.18 (d, J=7 Hz, 1H), 8.13 (s, 1H), 7.56 (d, J=7 Hz, 1H), 7.29 (t, J=8 Hz, 1H), 6.37 (m, 2H), 6.29 (s, 1H), 5.82 (d, J=7 Hz, 1H), 5.41 (s, 1H), 5.25 (t, J=7 Hz, 1H), 3.83 (s, 3H), 3.75 (m, 4H), 3.67 (s, 2H), 3.17 (s, 1H), 2.94 (s, 1H), 2.83 (d, J=7 Hz, 1H), 2.58 (m, 4H), 2.36 (d, J=7 Hz, 1H). MS: 509.2 (M+H). HPLC retention time: 1.71 minutes (G Method).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-dc2afd2c0a0041fa96fdc8f51a3562e1
Source dataset
uspto-grants-2016_01
Patent number
US09238656B2

Reaction notes

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