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Diisopropylethylamine → 2-chloro-7-(2,4-difluorophenyl)-N-(3-(2-(3-methyl-1H-1,2,4-triazol-1-yl)-5-nitrophenoxy)propyl)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-amine

HRID 474270
Notes
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Reaction equation

HRID 474270 reaction equation
[Cl:1][C:2]1[N:3]=[C:4](Cl)[C:5]2[CH2:10][CH2:9][CH:8]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][C:12]=3[F:18])[C:6]=2[N:7]=1.C(N(C(C)C)CC)(C)C.[CH3:29][C:30]1[N:34]=[CH:33][N:32]([C:35]2[CH:45]=[CH:44][C:43]([N+:46]([O-:48])=[O:47])=[CH:42][C:36]=2[O:37][CH2:38][CH2:39][CH2:40][NH2:41])[N:31]=1>C(#N)C>[Cl:1][C:2]1[N:3]=[C:4]([NH:41][CH2:40][CH2:39][CH2:38][O:37][C:36]2[CH:42]=[C:43]([N+:46]([O-:48])=[O:47])[CH:44]=[CH:45][C:35]=2[N:32]2[CH:33]=[N:34][C:30]([CH3:29])=[N:31]2)[C:5]2[CH2:10][CH2:9][CH:8]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][C:12]=3[F:18])[C:6]=2[N:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 580755852,4-Dichloro-7-(2,4-difluorophenyl)-6,7-dihydro-5H-cyclopenta[D]pyrimidineHCID 666658793-(2-(3-methyl-1H-1,2,4-triazol-1-yl)-5-nitrophenoxy)propan-1-amine

Product 1

HCID 866681152-chloro-7-(2,4-difluorophenyl)-N-(3-(2-(3-methyl-1H-1,2,4-triazol-1-yl)-5-nitrophenoxy)propyl)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-amineYield 55.4%

Reagents, catalysts & solvents

1
HCID 6342AcetonitrileSolvent

Procedure

To a solution of 2,4-dichloro-7-(2,4-difluorophenyl)-6,7-dihydro-5H-cyclopenta[d]pyrimidine (Preparation T, 0.717 g, 2.38 mmol) in acetonitrile (40 mL) was added diisopropylethylamine (0.420 g, 3.25 mmol) followed by 3-(2-(3-methyl-1H-1,2,4-triazol-1-yl)-5-nitrophenoxy)propan-1-amine (Preparation K, 0.60 g, 2.164 mmol) at room temperature. The reaction mixture was stirred at room temperature for 18 h. The solvent was removed under reduced pressure and the residue was taken in dichloromethane (10 mL) and silica (2 g). The resultant slurry of the compound on silica was subjected to flash chromatography using a Teledyne Isco instrument (12 g RediSep silica column, 50% ethyl acetate in pet-ether) to get 2-chloro-7-(2,4-difluorophenyl)-N-(3-(2-(3-methyl-1H-1,2,4-triazol-1-yl)-5-nitrophenoxy)propyl)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-amine (0.65 g, 55.4%) as a light yellow solid. LC-MS (M+H)+=542.0. 1H NMR (400 MHz, CDCl3) δ ppm 8.95 (1H, s), 8.05-7.93 (3H, m), 6.95-6.77 (3H, m), 4.86 (1H, br s), 4.86-4.85 (1H, m), 4.37-4.34 (2H, m), 3.75-3.75 (2H, s), 2.69-2.50 (3H, m), 2.50 (3H, s), 2.29-2.26 (2H, m), 2.01-1.98 (1H, m).

Workup

  1. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-115c6a4fdf1a4330a0c50545c08f5048
Source dataset
uspto-grants-2014_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08637523B2

Reaction notes

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