Methyl Isocyanate → 1-[2-(2,6-Dichlorophenyl)-2H-pyrazolo[4,3-c]pyridine-4-yl]-3-methylurea

HRID 626667Notes

Reaction equation

HRID 626667 reaction equation
CO[C:3](=[O:22])[NH:4][C:5]1[C:10]2=[CH:11][N:12]([C:14]3[C:19]([Cl:20])=[CH:18][CH:17]=[CH:16][C:15]=3[Cl:21])[N:13]=[C:9]2[CH:8]=[CH:7][N:6]=1.ClC1C=CC=C(Cl)[C:25]=1[N:31]1C=C2C(N)=NC=CC2=N1.CN=C=O>>[Cl:21][C:15]1[CH:16]=[CH:17][CH:18]=[C:19]([Cl:20])[C:14]=1[N:12]1[CH:11]=[C:10]2[C:5]([NH:4][C:3]([NH:31][CH3:25])=[O:22])=[N:6][CH:7]=[CH:8][C:9]2=[N:13]1

Participants

4

Reactant 3

HCID 12228Methyl IsocyanateHCID 696711782-(2,6-Dichlorophenyl)-2h-pyrazolo[4,3-c]pyridin-4-amineHCID 69671452[2-(2,6-Dichlorophenyl)-2H-pyrazolo[4,3-c]pyridine-4-yl]carbamic acid methyl ester

Product 1

HCID 696712681-[2-(2,6-Dichlorophenyl)-2H-pyrazolo[4,3-c]pyridine-4-yl]-3-methylureaYield 78%

Procedure

Following the procedure described for [2-(2,6-dichlorophenyl)-2H-pyrazolo[4,3-c]pyridine-4-yl]carbamic acid methyl ester, 2-(2,6-dichlorophenyl)-2H-pyrazolo[4,3-c]pyridine-4-ylamine and methyl isocyanate were reacted to afford the title compound as a white solid (78% yield). 1H NMR (400 MHz, DMSO-d6): δ 10.06 (br s, 1H), 9.75-9.70 (m, 1H), 9.04 (d, J=0.9 Hz, 1H), 7.85 (d, J=6.5 Hz, 1H), 7.83-7.76 (m, 2H), 7.70 (dd, J=9.0, 7.3 Hz, 1H), 7.17 (dd, J=6.5, 0.9 Hz, 1H), 2.84 (d, J=4.6 Hz, 3H). LCMS (Method B): RT=2.69 min, m/z: 336 [M+H+].

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-90bb69539c0849fdbdae6c826f211fbf
Source dataset
uspto-grants-2016_04
Patent number
US09309240B2

Reaction notes

Loading…