Pyrimidine-5-carboxaldehyde → HCID 178513983, compound

HRID 591986Notes

Reaction equation

HRID 591986 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[CH:26]=[C:25]([CH:27]=O)[CH:24]=[N:23][CH: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:27]([C:25]3[CH:26]=[N:21][CH:22]=[N:23][CH:24]=3)[NH:1][C:2]2=[N:3][CH:4]=1

Participants

3

Reactant 2

HCID 2761034Pyrimidine-5-carboxaldehydeHCID 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 178513983HCID 178513983, compoundYield 14.3%

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 Pyrimidine-5-carbaldehyde (17.6 mg, 0.163 mmol) were reacted to produce 9.0 mg (14%) of the title compound. mp: >300° C., 1H NMR (300 MHz, DMSO-d6): 13.7 (s, 1H), 9.42 (s, 2H), 9.28 (s, 1H), 8.10 (s, 1H), 7.77 (s, 1H), 7.35 (m, 1H), 7.23 (s, 1H), 6.39 (d, J=8 Hz, 1H), 5.22 (t, J=8 Hz, 1H), 3.3 (s, 1H), 2.90 (s, 1H), 2.78 (s, 1H), 2.63 (d, J=8 Hz, 1H), 2.25 (d, J=8 Hz, 1H), 1.40 (d, J=9 Hz, 1H). MS: 426, 428 (M+H), HPLC: 1.91 min (G method).

Sources & evidence

ORD record
ord-524dae150e1241f9b03906e176801c58
Source dataset
uspto-grants-2016_01
Patent number
US09238656B2

Reaction notes

Loading…