Triethylamine hydrochloride → HCID 178457754, compound

HRID 1623961Notes

Reaction equation

[C:1]([C:3]([NH:6][C:7]([C:9]1[C:10]2[CH2:11][C@H:12]3[CH2:24][C@H:13]3[C:14]=2[N:15]([C:17]2[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][N:18]=2)[N:16]=1)=[O:8])([CH3:5])[CH3:4])#[N:2].[N-:25]=[N+:26]=[N-:27].[Na+].Cl.C(N(CC)CC)C>CN(C=O)C>[CH3:4][C:3]([NH:6][C:7]([C:9]1[C:10]2[CH2:11][C@H:12]3[CH2:24][C@H:13]3[C:14]=2[N:15]([C:17]2[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][N:18]=2)[N:16]=1)=[O:8])([C:1]1[NH:27][N:26]=[N:25][N:2]=1)[CH3:5]

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of (1aR,5aR)-2-(4-chloro-pyridin-2-yl)-1a,2,5,5a-tetrahydro-1H-2,3-diaza-cyclopropa[a]pentalene-4-carboxylic acid (cyano-dimethyl-methyl)-amide (100 mg, 0.293 mmol), sodium azide (28.5 mg, 0.439 mmol) and triethylamine hydrochloride (81 mg, 0.585 mmol) in DMF (2 mL) was heated in a heavy-walled sealed tube under microwave irradiation at 110° C. for 1 h. Another 50 mg sodium azide and 150 mg triethylamine hydrochloride were added, and the mixture was heated under microwave for another 5 h at 125° C. The mixture was purified by prep HPLC to give the title compound as a white solid (33 mg). LCMS m/z=385.3 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ ppm 0.35 (td, J=4.4, 3.4 Hz, 1H), 1.23 (td, J=7.8, 4.6 Hz, 1H), 1.757 (s, 3H), 1.764 (s, 3H), 2.21-2.28 (m, 1H), 2.66 (d, J=16.6 Hz, 1H), 2.71-2.75 (m, 1H), 2.79 (dd, J=16.6, 6.4 Hz, 1H), 7.54 (dd, J=5.4, 1.9 Hz, 1H), 8.26 (d, J=1.9 Hz, 1H), 8.42 (bs, 1H), 8.51 (d, J=5.4 Hz, 1H), 16.0 (bs, 1H).

Workup

temperaturethe mixture was heated under microwave for another 5 h at 125° C
customThe mixture was purified by prep HPLC

Sources & evidence

ORD record: ord-2e53c0968d5f4cc4b73f36ca990fadf3
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08778950B2

Reaction notes

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