Triethylamine → HCID 66612100, compound

HRID 1621924Notes

Reaction equation

HRID 1621924 reaction equation
Cl[CH:2]([C:7]1[CH:8]=[C:9]([C:23]2[N:28]=[C:27]([CH3:29])[N:26]=[C:25]([N:30]([CH2:40][C:41]3[CH:46]=[CH:45][C:44]([O:47][CH3:48])=[CH:43][CH:42]=3)[CH2:31][C:32]3[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[CH:34][CH:33]=3)[N:24]=2)[C:10]([NH:13][C:14]2[CH:15]=[N:16][C:17]([O:21][CH3:22])=[C:18]([F:20])[CH:19]=2)=[N:11][CH:12]=1)[C:3]([F:6])([F:5])[F:4].[C:49]([N:56]1[CH2:61][CH2:60][NH:59][CH2:58][CH2:57]1)([O:51][C:52]([CH3:55])([CH3:54])[CH3:53])=[O:50].C(N(CC)CC)C>CC#N>[CH3:48][O:47][C:44]1[CH:43]=[CH:42][C:41]([CH2:40][N:30]([CH2:31][C:32]2[CH:33]=[CH:34][C:35]([O:38][CH3:39])=[CH:36][CH:37]=2)[C:25]2[N:26]=[C:27]([CH3:29])[N:28]=[C:23]([C:9]3[CH:8]=[C:7]([CH:2]([N:59]4[CH2:58][CH2:57][N:56]([C:49]([O:51][C:52]([CH3:55])([CH3:54])[CH3:53])=[O:50])[CH2:61][CH2:60]4)[C:3]([F:4])([F:6])[F:5])[CH:12]=[N:11][C:10]=3[NH:13][C:14]3[CH:15]=[N:16][C:17]([O:21][CH3:22])=[C:18]([F:20])[CH:19]=3)[N:24]=2)=[CH:46][CH:45]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 66611809HCID 66611809, compound

Product 1

HCID 66612100HCID 66612100, compoundYield 96.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 4-(5-(1-chloro-2,2,2-trifluoroethyl)-2-(5-fluoro-6-methoxypyridin-3-ylamino)pyridin-3-yl)-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine (1.059 g, 1.548 mmol) in CH3CN (10.00 mL) was treated with 1-N-Boc-piperazine (Aldrich, 0.577 g, 3.10 mmol) and triethylamine (1.079 mL, 7.74 mmol) and the mixture was heated at 100° C. for 3 h. The reaction mixture was concentrated and the crude product was adsorbed onto a plug of silica gel and chromatographed through a silica gel column (100% DCM to 5% MeOH (w/NH3 in DCM) to give tert-butyl 4-(1-(5-(4-(bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)-6-(5-fluoro-6-methoxypyridin-3-ylamino)pyridin-3-yl)-2,2,2-trifluoroethyl)piperazine-1-carboxylate (1.24 g, 1.487 mmol, 96% yield) as a brown foam. m/z (ESI, +ve ion) 834 (M+H)+.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customchromatographed through a silica gel column (100% DCM to 5% MeOH (w/NH3 in DCM)

Sources & evidence

ORD record
ord-f0433c38bbbf4e59b8010ffbad6646c1
Source dataset
uspto-grants-2014_07
Patent number
US08772480B2

Reaction notes

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