2-Pyrazol-1-yl-benzaldehyde → HCID 178513966, compound

HRID 591983Notes

Reaction equation

HRID 591983 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[CH:33]=[CH:32][CH:31]=[CH:30][C:27]=2[CH:28]=O)[CH:25]=[CH:24][CH:23]=[N: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:28]([C:27]3[CH:30]=[CH:31][CH:32]=[CH:33][C:26]=3[N:21]3[CH:25]=[CH:24][CH:23]=[N:22]3)[NH:1][C:2]2=[N:3][CH:4]=1

Participants

3

Reactant 2

HCID 9658662-Pyrazol-1-yl-benzaldehydeHCID 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 178513966HCID 178513966, compoundYield 45.5%

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-Pyrazol-1-yl-benzaldehyde (28 mg, 0.163 mmol) were reacted to produce 33 mg (45%) of the title compound. mp: 120° C., 1H NMR (300 MHz, DMSO-d6): 12.88 (s, 1H), 8.00 (s, 1H), 7.82 (d, J=8 Hz, 1H), 7.77 (s, 1H), 7.66 (m, 3H), 7.60 (m, 1H), 7.57 (s, 1H), 7.16 (s, 1H), 7.04 (d, J=8 Hz, 1H), 6.37 (s, 1H), 6.22 (s, 1H), 6.10 (s, 1H), 4.87 (t, J=8 Hz, 1H), 3.32 (s, 1H), 2.80 (s, 1H), 2.16 (d, J=8 Hz, 1H), 1.31 (d, J=8 Hz, 1H). MS: 490, 492 (M+H), HPLC: 2.28 min (G method).

Sources & evidence

ORD record
ord-fe87ff1c7fbd4dbe8d4eb2a8f8a00916
Source dataset
uspto-grants-2016_01
Patent number
US09238656B2

Reaction notes

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