4-(Trifluoromethoxy)benzene-1,2-diamine → HCID 178480879, compound

HRID 646987Notes

Reaction equation

HRID 646987 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([O:10][CH2:11][CH2:12][CH2:13][N:14]2[CH2:19][CH2:18][N:17]([CH3:20])[CH2:16][CH2:15]2)[CH:7]=[CH:6][C:3]=1[CH:4]=O.[F:21][C:22]([F:33])([F:32])[O:23][C:24]1[CH:25]=[C:26]([NH2:31])[C:27]([NH2:30])=[CH:28][CH:29]=1>>[Cl:1][C:2]1[CH:9]=[C:8]([O:10][CH2:11][CH2:12][CH2:13][N:14]2[CH2:19][CH2:18][N:17]([CH3:20])[CH2:16][CH2:15]2)[CH:7]=[CH:6][C:3]=1[C:4]1[NH:30][C:27]2[CH:28]=[CH:29][C:24]([O:23][C:22]([F:21])([F:32])[F:33])=[CH:25][C:26]=2[N:31]=1

Participants

3

Reactant 2

HCID 27739594-(Trifluoromethoxy)benzene-1,2-diamineHCID 575254242-Chloro-4-[3-(4-methylpiperazin-1-yl)propoxy]benzaldehyde

Product 1

HCID 178480879HCID 178480879, compoundYield 24.8%

Procedure

This compound was prepared by the method described in General Procedure 3 using 2-chloro-4-[3-(4-methyl-piperazin-1-yl)-propoxy]-benzaldehyde (200 mg, 0.68 mmol, 1.0 equiv), 4-trifluoromethoxy-benzene-1,2-diamine (119 mg, 0.62 mmol, 0.92 equiv) and Na2S2O5 (167 mg, 0.88 mmol, 1.3 equiv). Purification by Method 2 afforded 72 mg (23%) of the title compound. MS (electrospray): mass calculated for C22H24ClF3N4O2, 468.15; m/z found, 469.4 [M+H]+. 1H NMR (400 MHz, CD3OD): 7.82 (d, J=8.7 Hz, 1H), 7.69 (d, J=8.8 Hz, 1H), 7.55 (s, 1H), 7.23 (d, J=8.5 Hz, 1H), 7.21 (d, J=1.6 Hz, 1H), 7.1 (dd, J=8.6, 2.2 Hz, 1H), 4.17 (t, J=5.7 Hz, 2H), 2.88-2.38 (m, 10H), 2.32 (s, 3H), 2.10-1.95 (m, 2H).

Workup

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

Sources & evidence

ORD record
ord-6f0a14857aae43559d7824b5b3e6927b
Source dataset
uspto-grants-2010_04
Patent number
US07705143B2

Reaction notes

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