3,4-Diaminotoluene → HCID 178423451, compound

HRID 646993Notes

Reaction equation

HRID 646993 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][CH2:10][O:11][C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15]([CH:22]=O)=[CH:14][CH:13]=2)[CH2:4][CH2:3]1.[CH3:24][C:25]1[CH:26]=[C:27]([NH2:32])[C:28]([NH2:31])=[CH:29][CH:30]=1>>[CH3:24][C:25]1[CH:30]=[CH:29][C:28]2[NH:31][C:22]([C:15]3[C:16]4[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=4)[C:12]([O:11][CH2:10][CH2:9][CH2:8][N:5]4[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]4)=[CH:13][CH:14]=3)=[N:32][C:27]=2[CH:26]=1

Participants

3

Reactant 2

HCID 103323,4-DiaminotolueneHCID 57525430HCID 57525430, compound

Product 1

HCID 178423451HCID 178423451, compound

Procedure

This compound was prepared by the method described in Example 1, using 4-[3-(4-methyl-piperazin-1-yl)-propoxy]-naphthalene-1-carbaldehyde (63 mg, 0.20 mmol, 1.0 equiv), 4-methyl-benzene-1,2-diamine (24 mg, 0.20 mmol, 1.0 equiv), and Na2S2O5 (49 mg, 0.26 mmol, 1.3 equiv) in General Procedure 3. The desired product was isolated from the reaction mixture using Method 1 and was subsequently re-purified by Method 2 to afford 54.6 mg (66%) of the title compound. MS (electrospray): mass calculated for C26H30N4O, 414.24; m/z found, 415.62 [M+H]+. 1H NMR (400 MHz, CD3OD): 8.48 (d, J=8.0 Hz, 1H), 8.10 (d, J=8.4 Hz, 1H), 8.0 (d, J=8.2 Hz, 1H), 7.78-7.65 (m, 4H), 7.50 (d, J=8.4 Hz, 1H), 7.21 (d, J=8.2 Hz, 1H), 4.43 (t, J=6.0 Hz, 2H), 3.40 (br s, 4H), 3.30-3.00 (m, 6H), 2.88 (s, 3H), 2.59 (s, 3H), 2.36-2.30 (m, 2H).

Workup

  1. customThis compound was prepared by the method

Sources & evidence

ORD record
ord-569a224f2e1a4d56a4811cd0481246a2
Source dataset
uspto-grants-2010_04
Patent number
US07705143B2

Reaction notes

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