1-Methyl-1H-pyrrole-2-carbaldehyde → HCID 178480149, compound

HRID 591988Notes

Reaction equation

HRID 591988 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]=[CH:25][CH:24]=[C:23]1[CH:27]=O>>[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:23]3[N:22]([CH3:21])[CH:26]=[CH:25][CH:24]=3)[NH:1][C:2]2=[N:3][CH:4]=1

Participants

3

Reactant 2

HCID 145041-Methyl-1H-pyrrole-2-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 178480149HCID 178480149, compoundYield 60.1%

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 1-Methyl-1H-pyrrole-2-carbaldehyde (17.7 mg, 0.163 mmol) were reacted to produce 38 mg (60%) of the title compound. mp: 293-295° C., 1H NMR (300 MHz, DMSO-d6): 12.89 (s, 1H), 7.97 (s, 1H), 7.71 (s, 1H), 7.21 (s, 1H), 6.97 (s, 1H), 6.93 (br s, 2H), 6.35 (s, 1H), 6.28 (s, 1H), 6.14 (s, 1H), 5.26 (t, J=8 Hz, 1H), 4.05 (s, 3H), 3.32 (s, 1H), 3.29 (s, 1H), 2.85 (s, 1H), 2.73 (s, 1H), 2.59 (d, J=8 Hz, 1H), 2.26 (d, J=8 Hz, 1H), 1.40 (d, J=8 Hz, 1H). MS: 427, 429 (M+H), HPLC: 2.40 (G method).

Sources & evidence

ORD record
ord-17d92e525f144492ae0d28122f12558f
Source dataset
uspto-grants-2016_01
Patent number
US09238656B2

Reaction notes

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