2H-Pyran, 4-chlorotetrahydro- → HCID 59752670, compound

HRID 749918Notes

Reaction equation

HRID 749918 reaction equation
C(OC([N:8]1[CH2:17][CH2:16][C:15]2[NH:14][N:13]=[C:12]([C:18]3[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=3)[C:11]=2[CH2:10][CH2:9]1)=O)(C)(C)C.Cl[CH:26]1[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1.ClC1C=CC(C2C3CCNCCC=3NN2C2CCOCC2)=CC=1>>[Cl:24][C:21]1[CH:20]=[CH:19][C:18]([C:12]2[C:11]3[CH2:10][CH2:9][NH:8][CH2:17][CH2:16][C:15]=3[N:14]([CH:26]3[CH2:31][CH2:30][O:29][CH2:28][CH2:27]3)[N:13]=2)=[CH:23][CH:22]=1

Participants

4

Reactant 3

HCID 1372022H-Pyran, 4-chlorotetrahydro-HCID 672690203-(4-chloro-phenyl)-4,5,7,8-tetrahydro-1H-1,2,6-triaza-azulene-6-carboxylic acid tert-butyl esterHCID 67269571HCID 67269571, compound

Product 1

HCID 59752670HCID 59752670, compound

Procedure

The title compound was prepared from 3-(4-chloro-phenyl)-4,5,7,8-tetrahydro-1H-1,2,6-triaza-azulene-6-carboxylic acid tert-butyl ester (Example 103, Step B; 0.40 mmol) using 4-chloro-tetrahydro-pyran (1.5 mmol) in place of chloro-cyclobutane. The title compound was obtained as a 2:1 mixture (10 mg) with 3-(4-chloro-phenyl)-2-(tetrahydro-pyran-4-yl)-1,4,5,6,7,8-hexahydro-1,2,6-triaza-azulene. Data for the mixture: MS (ESI): exact mass calculated for C18H22ClN3O, 331.15; found, m/z 332.4 [M+H]+. 1H NMR (500 MHz, CD3OD): 7.44-7.42 (m, 1H), 7.36-7.30 (m, 4H), 7.20-7.18 (m, 1H), 4.36-4.33 (m, 1H), 3.97-3.94 (m, 3H), 3.87-3.86 (m, 1H), 3.51-3.49 (m, 3H), 3.28-3.25 (m, 1H), 2.90-2.75 (m, 8H), 2.66-2.64 (m, 2H), 2.39-2.37 (m, 1H), 2.19-2.10 (m, 3H), 1.74-1.71 (m, 2H), 1.65-1.62 (m, 1H).

Sources & evidence

ORD record
ord-f80ac274d86e467d95be2c9f13736ff7
Source dataset
uspto-grants-2008_07
Patent number
US07402680B2

Reaction notes

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