1-Methyl-1H-pyrazole-4-carbaldehyde → HCID 178480120, compound

HRID 591969Notes

Reaction equation

HRID 591969 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.[CH3:21][N:22]1[CH:26]=[C:25]([CH:27]=O)[CH:24]=[N:23]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:24]=[N:23][N:22]([CH3:21])[CH:26]=3)[NH:1][C:2]2=[N:3][CH:4]=1

Participants

3

Reactant 2

HCID 5731171-Methyl-1H-pyrazole-4-carbaldehydeHCID 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 178480120HCID 178480120, compoundYield 45.5%

Procedure

In a similar fashion to Compound LXXVI, (1S,2S,3R,4R)-3-(2,3-Diamino-5-bromo-pyridin-4-ylamino)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid amide (40.0 mg, 0.118 mmol) and 1-methyl-1H-pyrazole-4-carbaldehyde (14.3 mg, 0.130 mmol) were reacted to produce 23 mg (45%) of the title compound. mp: 255-258° C., 1H NMR (300 MHz, DMSO-d6): 11.99 (s, 1H), 7.99 (d, J=8 Hz, 1H), 7.96 (s, 1H), 7.72 (s, 1H), 7.19 (s, 1H), 6.88 (d, J=8 Hz, 1H), 6.49 (d, J=8 Hz, 1H), 6.35 (m, 2H), 5.30 (t, J=8 Hz, 1H), 4.34 (m, 1H), 3.97 (s, 2H), 3.02 (s, 4H), 2.87 (s, 1H), 2.74 (s, 1H), 2.61 (d, J=8 Hz, 1H), 2.26 (d, J=8 Hz, 1H), 1.38 (d, J=8 Hz, 1H). MS: 428, 430 (M+H), HPLC: 1.94 min (G method).

Sources & evidence

ORD record
ord-926081cd27174090b28d892bdacadcd8
Source dataset
uspto-grants-2016_01
Patent number
US09238656B2

Reaction notes

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