2,3-Diaminotoluene → HCID 11406436, compound

HRID 646992Notes

Reaction equation

HRID 646992 reaction equation
[F: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.[CH3:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([NH2:28])[C:23]=1[NH2:29]>>[F:1][C:2]1[CH:3]=[C:4]([C:5]2[NH:28][C:24]3[CH:25]=[CH:26][CH:27]=[C:22]([CH3:21])[C:23]=3[N:29]=2)[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

Participants

3

Reactant 2

HCID 175932,3-DiaminotolueneHCID 57525429HCID 57525429, compound

Product 1

HCID 11406436HCID 11406436, compoundYield 100%

Procedure

This compound was prepared by the method described in Example 1, using 3-fluoro-4-[3-(4-methyl-piperazin-1-yl)-propoxy]-benzaldehyde (94 mg, 0.34 mmol, 1.0 equiv), 3-methyl-benzene-1,2-diamine (42 mg, 0.34 mmol, 1.0 equiv), and Na2S2O5 (84 mg, 0.44 mmol, 1.3 equiv) in General Procedure 3. Purification by Method 2 afforded 130 mg (100%) of the title compound. MS (electrospray): mass calculated for C22H27FN4O, 382.22; m/z found, 383.2 [M+H]+. 1H NMR (400 MHz, CD3OD): 7.86-7.78 (m, 2H), 7.40-7.37 (m, 1H), 7.12-6.97 (m, 3H), 3.99 (t, J=6.1 Hz, 2H), 3.00-2.30 (m, 13H), 2.25 (s, 3H), 1.94-1.90 (m, 2H).

Workup

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

Sources & evidence

ORD record
ord-4559e915d7fc42c3a7e8a9d31f1b86ff
Source dataset
uspto-grants-2010_04
Patent number
US07705143B2

Reaction notes

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