HCID 89726240, compound → HCID 178487552, compound

HRID 591949Notes

Reaction equation

HRID 591949 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.[OH:21][C@@H:22]([CH3:40])[CH2:23][N:24]1[CH2:29][CH2:28][CH:27]([C:30]2[CH:37]=[CH:36][C:33]([CH:34]=O)=[C:32]([O:38][CH3:39])[CH:31]=2)[CH2:26][CH2:25]1>>[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:34]([C:33]3[CH:36]=[CH:37][C:30]([CH:27]4[CH2:28][CH2:29][N:24]([CH2:23][C@@H:22]([OH:21])[CH3:40])[CH2:25][CH2:26]4)=[CH:31][C:32]=3[O:38][CH3:39])[NH:1][C:2]2=[N:3][CH:4]=1

Participants

3

Reactant 2

HCID 89726240HCID 89726240, 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 178487552HCID 178487552, 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 4-[1-((S)-2-hydroxypropyl)-piperidin-4-yl]-2-methoxy-benzaldehyde were reacted to produce the title compound (70%). 1H NMR (d-chloroform): 10.81 (br s, 1H), 8.33 (d, J=9 Hz, 1H), 8.01 (s, 1H), 7.03 (d, J=9 Hz, 1H), 6.94 (s, 1H), 6.42 (s, 1H), 6.35 (m, 2H), 5.55 (d, J=8 Hz, 1H), 5.27 (br s, 1H), 5.20 (t, J=9 Hz, 1H), 4.07 (s, 3H), 3.89 (m, 1H), 3.58 (m, 1H), 3.18 (m, 2H), 2.97 (d, J=11 Hz, 1H), 2.92 (s, 1H), 2.87 (d, J=11 Hz, 1H), 2.61 (m, 1H), 2.49-2.24 (m, 4H), 2.08 (t, J=11 Hz, 1H), 1.94-1.71 (m, 5H), 1.18 (d, J=7 Hz, 3H). MS: 551.2 (M+H). HPLC retention time: 1.84 minutes (G Method).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-df784540fcea42ff8c935e2923518030
Source dataset
uspto-grants-2016_01
Patent number
US09238656B2

Reaction notes

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