Dimethylcarbamoyl Chloride → 3-[4-fluoro-3-[2-oxo-2-[4-(1-phenyltetrazol-5-yl)piperazin-1-yl]acetyl]-1H-pyrrolo[2,3-c]pyridin-7-yl]-1,1-dimethyl-urea

HRID 1157291Notes

Reaction equation

[NH2:1][C:2]1[N:3]=[CH:4][C:5]([F:32])=[C:6]2[C:10]([C:11](=[O:31])[C:12]([N:14]3[CH2:19][CH2:18][N:17]([C:20]4[N:24]([C:25]5[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=5)[N:23]=[N:22][N:21]=4)[CH2:16][CH2:15]3)=[O:13])=[CH:9][NH:8][C:7]=12.[CH3:33][N:34]([CH3:38])[C:35](Cl)=[O:36]>N1C=CC=CC=1>[F:32][C:5]1[CH:4]=[N:3][C:2]([NH:1][C:35](=[O:36])[N:34]([CH3:38])[CH3:33])=[C:7]2[NH:8][CH:9]=[C:10]([C:11](=[O:31])[C:12](=[O:13])[N:14]3[CH2:15][CH2:16][N:17]([C:20]4[N:24]([C:25]5[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=5)[N:23]=[N:22][N:21]=4)[CH2:18][CH2:19]3)[C:6]=12

Participants

Conditions

Temperature: 50 °C

Procedure

1-(7-amino-4-fluoro-1H-pyrrolo[2,3-c]pyridin-3-yl)-2-(4-(1-phenyl-1H-tetrazol-5-yl)piperazin-1-yl)ethane-1,2-dione (100 mg, 0.23 mmol) was dissolved in pyridine (1 mL). Dimethylcarbamyl chloride (0.21 mL, 2.3 mmol) was added and the mixture was heated at 50° C. for 18 h. Solvent was removed in vacuum and the residue was purified using reverse phase prep HPLC to afford the title compound as a pale tan solid (10 mg). 1HNMR (500 MHz, DMSO-D6) δ 8.89 (s, 1H), 8.25 (s, 1H), 7.70-7.59 (m, 5H), 3.67 (m, 2H), 3.44 (m, 2H), 3.37 (m, 2H), 3.20 (m, 2H), 3.11 (s, 3H), 2.88(s, 3H). LCMS: m/e 507 (M+H)+, ret time 1.04 min (method 3).

Workup

customSolvent was removed in vacuum
customthe residue was purified

Sources & evidence

ORD record: ord-b44b99762ecc4fb3afb6666dd3cc5385
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07807671B2

Reaction notes

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