1-Bromo-2-methylpropane → HCID 11415448, compound

HRID 2106260Notes

Reaction equation

HRID 2106260 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.[CH2:25](Br)[CH:26]([CH3:28])[CH3:27].C(OC(N1CCC2C(=C(C3C=CC(Cl)=CC=3)N(CC(C)C)N=2)CC1)=O)(C)(C)C>>[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]([CH2:25][CH:26]([CH3:28])[CH3:27])[N:13]=2)=[CH:23][CH:22]=1

Participants

4

Reactant 3

HCID 65551-Bromo-2-methylpropaneHCID 672690203-(4-chloro-phenyl)-4,5,7,8-tetrahydro-1H-1,2,6-triaza-azulene-6-carboxylic acid tert-butyl esterHCID 67269810HCID 67269810, compound

Product 1

HCID 11415448HCID 11415448, compoundYield 51%

Procedure

The title compound (0.031 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 isobutyl bromide (0.3 mmol) in place of 2-chloromethyl-thiophene. The reaction sequence also yielded 3-(4-chloro-phenyl)-2-isobutyl-4,5,7,8-tetrahydro-2H-1,2,6-triaza-azulene-6-carboxylic acid tert-butyl ester from the alkylation step. MS (ESI): exact mass calculated for C17H22ClN3, 303.15; found, m/z 304.1 [M+H]+. 1H NMR (500 MHz, CD3OD): 7.64 (d, J=6.6 Hz, 2H), 7.56 (d, J=6.6 Hz, 2H), 4.20 (d, J=7.4 Hz, 2H), 3.72-3.69 (br m, 2H), 3.62-3.60 (br m, 2H), 3.44-3.42 (br m, 2H), 3.29-3.27 (br m, 2H), 2.35 (m, 1H), 1.14 (d, J=6.7 Hz, 6H).

Sources & evidence

ORD record
ord-71054185a27d454781f0567c93a8ed4a
Source dataset
uspto-grants-2009_08
Patent number
US07579470B2

Reaction notes

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