Ethylenediamine → HCID 71255279, compound

HRID 540308Notes

Reaction equation

HRID 540308 reaction equation
[CH2:1]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[CH2:5][CH2:4][CH2:3][NH:2]1.Cl[C:13]1[CH:22]=[C:21](Cl)[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]=1.[CH3:24][NH:25][CH2:26][CH2:27][NH2:28].ClC1C=C(Cl)C2C(=CC=C(Cl)C=2)N=1.C(N)CN>>[CH3:24][NH:25][CH2:26][CH2:27][NH:28][C:21]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]=[C:13]([N:2]2[CH2:3][CH2:4][CH2:5][C:6]3[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=3[CH2:1]2)[CH:22]=1

Participants

6

Reactant 5

HCID 3301EthylenediamineHCID 8014N-MethylethylenediamineHCID 6075032,4-DichloroquinolineHCID 104644722,3,4,5-Tetrahydro-1H-benzo[c]azepineHCID 187966912,4,6-Trichloroquinoline

Product 1

HCID 71255279HCID 71255279, compound

Procedure

The title compound was prepared in analogy to Example 118-1 in Scheme 59 by using 2,3,4,5-tetrahydro-1H-2-benzazepine (commercial available), 2,4-dichloroquinoline (commercial available) and N-methyl-ethane-1,2-diamine (commercial available) instead of 7-bromo-2,3,4,5-tetrahydro-1H-2-benzazepine, 2,4,6-trichloroquinoline and ethane-1,2-diamine respectively. MS obsd. (ESI+) [(M+H)+] 347. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.42 (brs, 2 H), 7.88 (s, 1 H), 7.55 (d, J=6.4 Hz, 1 H), 7.47 (s, 2 H), 7.16-7.11 (m, 4 H), 6.01 (s, 1 H), 4.87 (s, 2 H), 4.14 (s, 2 H), 3.63 (s, 2 H), 3.20 (t, J=5.6 Hz, 2 H), 3.02 (s, 2 H), 2.67 (s, 3 H), 1.80 (s, 2 H).

Sources & evidence

ORD record
ord-48c27dae38754038a1f5b8107522f2ac
Source dataset
uspto-grants-2014_10
Patent number
US08871756B2

Reaction notes

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