1,3-Benzodioxole, 5-(chloromethyl)- → HCID 11406418, compound

HRID 749779Notes

Reaction equation

HRID 749779 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.[O:25]1[C:29]2[CH:30]=[CH:31][C:32]([CH2:34]Cl)=[CH:33][C:28]=2[O:27][CH2:26]1.C(OC(N1CCC2C(=C(C3C=CC(Cl)=CC=3)N(CC3C=CC4OCOC=4C=3)N=2)CC1)=O)(C)(C)C>>[O:25]1[C:29]2[CH:30]=[CH:31][C:32]([CH2:34][N:14]3[C:15]4[CH2:16][CH2:17][NH:8][CH2:9][CH2:10][C:11]=4[C:12]([C:18]4[CH:19]=[CH:20][C:21]([Cl:24])=[CH:22][CH:23]=4)=[N:13]3)=[CH:33][C:28]=2[O:27][CH2:26]1

Participants

4

Reactant 3

HCID 887131,3-Benzodioxole, 5-(chloromethyl)-HCID 672690203-(4-chloro-phenyl)-4,5,7,8-tetrahydro-1H-1,2,6-triaza-azulene-6-carboxylic acid tert-butyl esterHCID 67269867HCID 67269867, compound

Product 1

HCID 11406418HCID 11406418, compoundYield 45.8%

Procedure

The title compound (0.035 g) 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; 0.2 mmol) using benzo[1,3]dioxol-5-ylmethyl chloride (0.3 mmol) in place of 2-chloromethyl-thiophene. The reaction sequence also yielded 2-benzo[1,3]dioxol-5-ylmethyl-3-(4-chloro-phenyl)-4,5,7,8-tetrahydro-2H-1,2,6-triaza-azulene-6-carboxylic acid tert-butyl ester in the alkylation step. MS (ESI): exact mass calculated for C21H20ClN3O2, 381.12; found, m/z 382.1 [M+H]+. 1H NMR (500 MHz, CD3OD): 7.39-7.32 (m, 4H), 6.67-6.65 (m, 1H), 6.54-6.61 (m, 2H), 5.81 (s, 2H), 5.16 (s, 2H), 2.81-2.79 (m, 4H), 2.76-2.74 (m, 2H), 2.68-2.66 (m, 2H).

Sources & evidence

ORD record
ord-65e509e5f50545d78b80622d0f745f6e
Source dataset
uspto-grants-2008_07
Patent number
US07402680B2

Reaction notes

Loading…