N,N-Dimethylaminoethyl chloride hydrochloride → HCID 59752578, compound

HRID 749920Notes

Reaction equation

HRID 749920 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.Cl[CH2:27][CH2:28][N:29]([CH3:31])[CH3:30].ClC1C=CC(C2N(CCN(C)C)N=C3C=2CCNCC3)=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]([CH2:27][CH2:28][N:29]([CH3:31])[CH3:30])[N:13]=2)=[CH:23][CH:22]=1

Participants

4

Reactant 3

HCID 11636816N,N-Dimethylaminoethyl chloride hydrochlorideHCID 672690203-(4-chloro-phenyl)-4,5,7,8-tetrahydro-1H-1,2,6-triaza-azulene-6-carboxylic acid tert-butyl esterHCID 67269599HCID 67269599, compound

Product 1

HCID 59752578HCID 59752578, 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; 0.33 mmol) using (2-chloro-ethyl)-dimethyl-amine hydrogen chloride (0.66 mmol) in place of chloro-cyclobutane. The title compound was obtained as a 2:1 mixture (10 mg) with {2-[3-(4-chloro-phenyl)-5,6,7,8-tetrahydro-4H-1,2,6-triaza-azulen-2-yl]-ethyl}-dimethyl-amine. Data for the mixture: MS (ESI): exact mass calculated for C17H23ClN4, 318.16; found, m/z 319.4 [M+H]+. 1H NMR (500 MHz, CD3OD): 7.50-7.45 (m, 2H), 7.37-7.33 (m, 2H), 4.51-4.49 (m, 1.3H), 4.27-4.26 (m, 0.7H), 3.63-3.61 (m, 1.3H), 3.48-3.42 (m, 2H), 3.33-3.29 (m, 2H), 3.24-3.23 (m, 2H), 3.14-3.12 (m, 0.7H), 3.00-2.98 (m, 1.3H), 2.91 (s, 4H), 2.84 (s, 2H), 2.75-2.73 (m, 0.7H).

Sources & evidence

ORD record
ord-306864f73a8343b995c328da4a415b71
Source dataset
uspto-grants-2008_07
Patent number
US07402680B2

Reaction notes

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