HCID 89725965, compound → HCID 178495750, compound

HRID 591996Notes

Reaction equation

HRID 591996 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]([CH2:40][O:41][CH3:42])[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[CH2:26][CH2:25][N:24]([CH2:23][C@H:22]([OH:21])[CH2:40][O:41][CH3:42])[CH2:29][CH2:28]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 89725965HCID 89725965, 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 178495750HCID 178495750, compoundYield 47.1%

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 (109 mg, 0.373 mmol) and 4-[1-((S)-2-Hydroxy-3-methoxy-propyl)-piperidin-4-yl]-2-methoxy-benzaldehyde (126 mg, 0.410 mmol) were reacted to produce 102 mg (47%) of the title compound. mp: 189-191° C., 1H NMR (300 MHz, CDCl3): 10.67 (s, 1H), 8.35 (d, J=8 Hz, 1H), 8.04 (s, 1H), 7.04 (d, J=8 Hz, 1H), 6.94 (s, 1H), 6.39-6.35 (m, 3H), 5.51 (d, J=8 Hz, 1H), 5.19 (t, J=8 Hz, 1H), 5.07 (s, 1H), 4.08 (s, 3H), 3.89 (m, 1H), 3.19 (s, 2H), 2.98 (d, 1H), 2.91 (s, 1H), 2.88 (d, J=8 Hz, 1H), 2.62 (m, 1H), 2.46-2.22 (m, 5H). MS: 581 (M+H), HPLC: 1.90 min (G method).

Sources & evidence

ORD record
ord-b480e0e83c974243999eda8ef65eae5f
Source dataset
uspto-grants-2016_01
Patent number
US09238656B2

Reaction notes

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