4-Tert-butylbenzene-1,2-diamine → HCID 178422999, compound

HRID 646996Notes

Reaction equation

HRID 646996 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH2:11][CH2:12][CH2:13][N:14]1[CH2:19][CH2:18][N:17]([CH3:20])[CH2:16][CH2:15]1)[CH:5]=O.[C:21]([C:25]1[CH:26]=[C:27]([NH2:32])[C:28]([NH2:31])=[CH:29][CH:30]=1)([CH3:24])([CH3:23])[CH3:22]>>[C:21]([C:25]1[CH:30]=[CH:29][C:28]2[NH:31][C:5]([C:4]3[CH:7]=[CH:8][C:9]([O:10][CH2:11][CH2:12][CH2:13][N:14]4[CH2:19][CH2:18][N:17]([CH3:20])[CH2:16][CH2:15]4)=[C:2]([CH3:1])[CH:3]=3)=[N:32][C:27]=2[CH:26]=1)([CH3:24])([CH3:22])[CH3:23]

Participants

3

Reactant 2

HCID 4327084-Tert-butylbenzene-1,2-diamineHCID 575254273-Methyl-4-[3-(4-methylpiperazin-1-yl)propoxy]benzaldehyde

Product 1

HCID 178422999HCID 178422999, compoundYield 81%

Procedure

This compound was prepared by the method described in Example 1, using 3-methyl-4-[3-(4-methyl-piperazin-1-yl)-propoxy]-benzaldehyde (516 mg, 1.87 mmol, 1.0 equiv), 4-tert-butyl-benzene-1,2-diamine (307 mg, 1.87 mmol, 1.0 equiv), and Na2S2O5 (461 mg, 2.43 mmol, 1.3 equiv) in General Procedure 3. Purification by Method 2 afforded 633 mg (81%) of the title compound. MS (electrospray): mass calculated for C26H36N4O, 420.29; m/z found, 421.5 [M+H]+. 1H NMR (400 MHz, CD3OD): 7.90-7.85 (m, 2H), 7.65-7.40 (m, 2H), 7.33 (d, J=8.5 Hz, 1H), 7.04 (d, J=8.1 Hz, 1H), 4.14-4.11 (m, 2H), 2.90-2.28 (m, 16H), 2.06-2.03 (m, 2H), 1.39 (s, 9H).

Workup

  1. customThis compound was prepared by the method
  2. customPurification by Method 2

Sources & evidence

ORD record
ord-4b618fbb1ea8451a89f7c252e49c9034
Source dataset
uspto-grants-2010_04
Patent number
US07705143B2

Reaction notes

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