3-Ethyl-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-ylamine → HCID 66829997, compound

HRID 1040719Notes

Reaction equation

HRID 1040719 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][CH2:9][CH2:10][C:11]([NH:13][CH3:14])=[O:12])[C:5]([Cl:15])=[CH:4][N:3]=1.[CH2:16]([N:18]1[CH2:24][CH2:23][C:22]2[CH:25]=[C:26]([NH2:29])[CH:27]=[CH:28][C:21]=2[CH2:20][CH2:19]1)[CH3:17].Cl.O1CCOCC1>C(O)(C)C>[Cl:15][C:5]1[C:6]([NH:8][CH2:9][CH2:10][C:11]([NH:13][CH3:14])=[O:12])=[N:7][C:2]([NH:29][C:26]2[CH:27]=[CH:28][C:21]3[CH2:20][CH2:19][N:18]([CH2:16][CH3:17])[CH2:24][CH2:23][C:22]=3[CH:25]=2)=[N:3][CH:4]=1

Participants

5

Reactant 3

HCID 189434013-Ethyl-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-ylamineHCID 204431481,4-Dioxane hydrochlorideHCID 79632510HCID 79632510, compound

Product 1

HCID 66829997HCID 66829997, compoundYield 23.9%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of 3-(2,5-Dichloro-pyrimidin-4-ylamino)-N-methyl-propionamide (35 mg, 0.14 mmol) in isopropanol (3 mL) was treated 3-Ethyl-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-ylamine (27 mg, 0.14 mmol) and 4N HCl/dioxane (0.035 mL, 0.14 mmol). The reaction was irradiated at 130° C. for a total of 20 minutes. A white precipitate formed in the reaction mixture, which was collected via vacuum filtration and triturated with acetonitrile (5 mL) to afford 3-[5-Chloro-2-(3-ethyl-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-ylamino)-pyrimidin-4-ylamino]-N-methyl-propionamide (13.5 mg) as the HCl salt. LC/MS (ESI)=403.02 (M+H), MP=206.1° C. 1H NMR (400 MHz, DMSO, d6) δ 10.51 (m, 1H), 10.05 (m, 1H), 8.12 (s, 1H), 7.88 (m, 1H), 7.59 (s, 1H), 7.42 (m, 1H), 7.17 (d, 1H, J=8.34 Hz), 3.62 (m, 7H), 3.29 (m, 2H), 3.17 (m, 2H), 2.93 (m, 2H), 2.59 (s, 3H), 2.45 (m, 2H), 1.27 (m, 3H).

Workup

  1. customThe reaction was irradiated at 130° C. for a total of 20 minutes
  2. customA white precipitate formed in the reaction mixture, which
  3. filtrationwas collected via vacuum filtration
  4. customtriturated with acetonitrile (5 mL)

Sources & evidence

ORD record
ord-eca40a19f056440586fb4b59c1cc97f5
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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