2-(1-pyrrolidinyl)nicotinaldehyde → HCID 178513978, compound

HRID 591984Notes

Reaction equation

HRID 591984 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]([Br:20])=[CH:4][N:3]=1.[N:21]1([C:26]2[C:31]([CH:32]=O)=[CH:30][CH:29]=[CH:28][N:27]=2)[CH2:25][CH2:24][CH2:23][CH2:22]1>>[Br: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:32]([C:31]3[C:26]([N:21]4[CH2:25][CH2:24][CH2:23][CH2:22]4)=[N:27][CH:28]=[CH:29][CH:30]=3)[NH:1][C:2]2=[N:3][CH:4]=1

Participants

3

Reactant 2

HCID 27947632-(1-pyrrolidinyl)nicotinaldehydeHCID 117701905(1S,2S,3R,4R)-3-(2,3-Diamino-5-bromo-pyridin-4-ylamino)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid amide

Product 1

HCID 178513978HCID 178513978, compoundYield 34%

Procedure

In a similar fashion to Compound LXXXVII, (1S,2S,3R,4R)-3-(2,3-Diamino-5-bromo-pyridin-4-ylamino)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid amide (50 mg, 0.148 mmol) and 2-Pyrrolidin-1-yl-pyridine-3-carbaldehyde (28.6 mg, 0.163 mmol) were reacted to produce 24 mg (34%) of the title compound. mp: 190° C., 1H NMR (300 MHz, DMSO-d6): 13.02 (s, 1H), 8.21 (m, 1H), 8.02 (s, 1H), 7.71 (d, J=8 Hz, 1H), 6.68 (s, 1H), 7.18 (s, 1H), 7.06 (d, J=8 Hz, 1H), 6.75 (t, 1H), 6.27 (m, 1H), 6.17 (m, 1H), 5.14 (t, J=8 Hz, 1H), 3.32 (s, 3H), 3.29 (s, 2H), 3.08 (m, 2H), 2.85 (s, 1H), 2.71 (s, 1H), 2.55 (d, J=8 Hz, 1H), 2.25 (d, J=8 Hz, 1H), 1.82 (m, 2H), 1.73 (m, 2H), 1.37 (d, J=8 Hz, 1H), 1.09 (t, J=8 Hz, 1H). MS: 494, 496 (M+H), HPLC: 3.19 min (G method).

Sources & evidence

ORD record
ord-7c0acf279ed34bc4a932e1295a779391
Source dataset
uspto-grants-2016_01
Patent number
US09238656B2

Reaction notes

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