1-(4-Bromophenyl)-4-methylpiperazine → HCID 49839131, compound

HRID 1890020Notes

Reaction equation

HRID 1890020 reaction equation
NC1N=C2C(O)=CC=CN2N=1.[NH2:12][C:13]1[N:31]=[C:16]2[C:17]([O:21][CH2:22][C:23]3[CH:30]=[CH:29][CH:28]=[CH:27][C:24]=3[C:25]#[N:26])=[CH:18][CH:19]=[CH:20][N:15]2[N:14]=1.Br[C:33]1[CH:38]=[CH:37][C:36]([N:39]2[CH2:44][CH2:43][N:42]([CH3:45])[CH2:41][CH2:40]2)=[CH:35][CH:34]=1>>[NH2:12][C:13]1[N:31]=[C:16]2[C:17]([O:21][CH2:22][C:23]3[CH:30]=[CH:29][CH:28]=[CH:27][C:24]=3[C:25]#[N:26])=[CH:18][CH:19]=[CH:20][N:15]2[N:14]=1.[CH3:45][N:42]1[CH2:43][CH2:44][N:39]([C:36]2[CH:35]=[CH:34][C:33]([NH:12][C:13]3[N:31]=[C:16]4[C:17]([O:21][CH2:22][C:23]5[CH:30]=[CH:29][CH:28]=[CH:27][C:24]=5[C:25]#[N:26])=[CH:18][CH:19]=[CH:20][N:15]4[N:14]=3)=[CH:38][CH:37]=2)[CH2:40][CH2:41]1

Participants

5

Reactant 3

HCID 118176751-(4-Bromophenyl)-4-methylpiperazineHCID 67481420HCID 67481420, compoundHCID 67481450HCID 67481450, compound

Product 2

HCID 49839131HCID 49839131, compoundHCID 67481420HCID 67481420, compound

Procedure

262 a) 2-(2-Amino-[1,2,4]triazolo[1,5-a]pyridin-8-yloxymethyl)-benzonitrile was prepared from 2-amino-[1,2,4]triazolo[1,5-a]pyridin-8-ol (0.200 g, 1.33 mmol) 2-bromomethyl-benzonitrile (0.274 mL, 1.40 mmol) in a manner analogous to Example 260c. Product was isolated as a white solid. 1H NMR (400 MHz, (D3C)2SO, δ, ppm): 8.21 (d, J=6.6 Hz, 1H), 7.94 (d, J=7.8 Hz, 1H), 7.78-7.76 (m, 2H), 7.62-7.58 (m, 1H), 7.07 (d, J=8.0 Hz, 1H), 6.81-6.78 (m, 1H), 5.94 (s, 2H), 5.44 (s, 2H). MS=266 (MH)+. 262 b) 2-{2-[4-(4-Methyl-piperazin-1-yl)-phenylamino]-[1,2,4]triazolo[1,5-a]pyridin-8-yloxymethyl}benzonitrile was prepared from 2-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-8-yloxymethyl)-benzonitrile (115.0 mg, 0.434 mmol) and 1-(4-bromo-phenyl)-4-methyl-piperazine (128 mg, 0.500 mmol) in a manner analogous to Example 2d. Product was isolated as a pale orange solid (0.101 g, 53%). MP=156-157° C. 1H NMR (400 MHz, (D3C)2SO, δ, ppm): 9.32 (s, 1H), 8.40 (d, J=6.5 Hz, 1H), 7.93 (d, J=7.8 Hz, 1H), 7.80 (d, J=4.5 Hz, 2H), 7.62-7.60 (m, 1H), 7.50 (d, J=8.9 Hz, 1H), 7.17 (d, J=8.5 Hz, 1H), 6.98-6.88 (m, 3H), 5.49 (s, 2H), 3.04-3.02 (m, 4H), 2.47-2.44 (m, 4H), 2.22 (s, 3H). MS=440 (MH)+.

Workup

  1. customProduct was isolated as a white solid

Sources & evidence

ORD record
ord-4adc0183aec14e4281e1cbf52fe05bcb
Source dataset
uspto-grants-2013_08
Patent number
US08501936B2

Reaction notes

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