Ethylenediamine → N-[(2-Amino-4,5-dihydro-1,3-oxazol-5-yl)methyl]-6-chloro-2-(1,3,4,5-tetrahydro-2H-2-benzazepin-2-yl)quinolin-4-amine

HRID 540328Notes

Reaction equation

HRID 540328 reaction equation
[NH2:1][CH2:2][CH:3]([OH:28])[CH2:4][NH:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([Cl:16])[CH:14]=2)[N:9]=[C:8]([N:17]2[CH2:23][CH2:22][CH2:21][C:20]3[CH:24]=[CH:25][CH:26]=[CH:27][C:19]=3[CH2:18]2)[CH:7]=1.[CH2:29]1C2C=CC=CC=2CCC[NH:30]1.NCC(O)CN.C(N)CN.NCC(O)CNC1C2C(=CC=CC=2)N=C(N2CCCC3C=CC=CC=3C2)C=1>>[NH2:30][C:29]1[O:28][CH:3]([CH2:4][NH:5][C:6]2[C:15]3[C:10](=[CH:11][CH:12]=[C:13]([Cl:16])[CH:14]=3)[N:9]=[C:8]([N:17]3[CH2:23][CH2:22][CH2:21][C:20]4[CH:24]=[CH:25][CH:26]=[CH:27][C:19]=4[CH2:18]3)[CH:7]=2)[CH2:2][N:1]=1

Participants

6

Reactant 5

HCID 3301EthylenediamineHCID 611571,3-Diamino-2-propanolHCID 104644722,3,4,5-Tetrahydro-1H-benzo[c]azepineHCID 71255197HCID 71255197, compoundHCID 71255574HCID 71255574, compound

Product 1

HCID 71255545N-[(2-Amino-4,5-dihydro-1,3-oxazol-5-yl)methyl]-6-chloro-2-(1,3,4,5-tetrahydro-2H-2-benzazepin-2-yl)quinolin-4-amine

Procedure

The title compound was prepared in analogy to Example 9-1 by using 1-amino-3-{6-chloro-[2-(1,3,4,5-tetrahydro-2H-2-benzazepin-2-yl)quinolin-4-yl]amino}propan-2-ol [It was prepared in Scheme 1 by using 2,3,4,5-tetrahydro-1H-2-benzazepine (commercial available) and 1,3-diamino-propan-2-ol (commercial available) instead of 7-bromo-2,3,4,5-tetrahydro-1H-2-benzazepine and ethane-1,2-diamine respectively.] instead of 1-amino-3-{[2-(1,3,4,5-tetrahydro-2H-2-benzazepin-2-yl)quinolin-4-yl]amino}propan-2-ol. MS obsd. (ESI+) [(M+H)+] 422. 1H NMR (400 MHz, CD3OD) δ ppm 8.17 (s, 1 H), 7.82 (d, J=8.8 Hz, 1 H), 7.69 (m, 1 H), 7.52 (s, 1 H), 7.22 (m, 3 H), 6.15 (s, 1 H), 5.42 (m, 1 H), 4.99 (s, 2 H), 4.11 (m, 3 H), 3.94 (d, J=5.6 Hz, 2 H), 3.77 (dd, J=9.6, 6.8 Hz, 1 H), 3.09 (m, 2 H), 2.00 (d, J=5.6 Hz, 2 H).

Workup

  1. customwas prepared in Scheme 1

Sources & evidence

ORD record
ord-222feb8bc0bd4cb187aab12db0958b92
Source dataset
uspto-grants-2014_10
Patent number
US08871756B2

Reaction notes

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