Diisopropylethylamine → HCID 86633863, compound

HRID 1040714Notes

Reaction equation

HRID 1040714 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([Cl:8])=[C:4](Cl)[N:3]=1.[CH2:10]([N:12]1[CH2:18][CH2:17][C:16]2[CH:19]=[C:20]([NH2:23])[CH:21]=[CH:22][C:15]=2[CH2:14][CH2:13]1)[CH3:11].C(N(CC)C(C)C)(C)C>C(O)(C)C>[Cl:1][C:2]1[N:3]=[C:4]([NH:23][C:20]2[CH:21]=[CH:22][C:15]3[CH2:14][CH2:13][N:12]([CH2:10][CH3:11])[CH2:18][CH2:17][C:16]=3[CH:19]=2)[C:5]([Cl:8])=[CH:6][N:7]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 2372592,4,5-TrichloropyrimidineHCID 189434013-Ethyl-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-ylamine

Product 1

HCID 86633863HCID 86633863, compoundYield 539.7%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
80 °C

Procedure

2,5,6-trichloropyrimidine (200 mg, 0.15 mmol) and 3-ethyl-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-ylamine (209 mg, 1.10 mmol) were mixed with N,N-diisopropylethylamine (211 mg, 1.63 mmol) in 8 mL isopropyl alcohol and heated at 80° C. for 24 hours. The reaction was concentrated and the organics were partitioned between dichloromethane and saturated sodium bicarbonate solution. The organic layer was separated, was dried (sodium sulfate), and was concentrated. Chromatography on silica (1% to 20% methanol:dichloromethane gradient elution) afforded 273 mg (74%) of (2,5-dichloro-pyrimidin-4-yl)-(3-ethyl-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-yl)-amine as a tan foam. MS: 338.55 (M+H).

Workup

  1. concentrationThe reaction was concentrated
  2. customthe organics were partitioned between dichloromethane and saturated sodium bicarbonate solution
  3. customThe organic layer was separated
  4. dry with materialwas dried (sodium sulfate)
  5. concentrationwas concentrated

Sources & evidence

ORD record
ord-607d7e4e81eb4d0ba4bff3e075abfdd1
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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