Hydrochloric Acid → HCID 16660814, compound

HRID 2097136Notes

Reaction equation

HRID 2097136 reaction equation
[CH3:1][NH:2][CH2:3][C:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[O:6][C:5]=1[CH3:13].[ClH:14].[O:15]1[CH2:20][CH2:19][NH:18][C:17]2[N:21]=[CH:22][C:23]([CH:25]=[CH:26][C:27]([OH:29])=O)=[CH:24][C:16]1=2.ON1C2C=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C.CN(C)CCCN=C=NCC.Cl>CN(C=O)C.C(Cl)Cl.CCOCC.O>[ClH:14].[O:15]1[CH2:20][CH2:19][NH:18][C:17]2[N:21]=[CH:22][C:23](/[CH:25]=[CH:26]/[C:27]([N:2]([CH3:1])[CH2:3][C:4]3[C:8]4[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=4[O:6][C:5]=3[CH3:13])=[O:29])=[CH:24][C:16]1=2

Participants

11

Reactant 6

HCID 313Hydrochloric AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 66967084Methyl(2-methylbenzofuran-3-ylmethyl)amineHCID 66967174HCID 66967174, compound

Product 1

HCID 16660814HCID 16660814, compoundYield 39%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl-(2-methyl-benzofuran-3-ylmethyl)-amine (159 mg, 0.91 mmol) in DMF (5 mL) were added in sequential order 3-(3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-7-yl)-acrylic acid hydrochloride (171 mg, 0.83 mmol), 1-hydroxybenzotriazole (127 mg, 0.91 mmol), diisopropylethylamine (289 uL, 1.06 mmol), and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide (182 mg, 0.91 mmol). The mixture was stirred at room temperature overnight, cooled in an ice bath and treated with water under rapid stirring. The resulting precipitate was collected by filtration, dried and triturated with diethyl ether to yield a pale yellow solid. The solid was re-solvated in methylene chloride (5 mL) and a solution of 2M HCl in ether (2 mL) was added to precipitate an orange solid. The precipitated solid was collected by filtration, dried and triturated with diethyl ether to yield the title compound (118 mg, 39%) as a mixture of amide rotamers. 1H NMR (400 MHz, DMSO-d6) δ 8.76 (1s, 1H), 7.93-7.97 (m, 1H), 7.47-7.59 (m, 3H), 7.12-7.27 (m, 3H), 4.73-4.94 (m, 2H), 4.27 (m, 2H), 3.59 (m, 5H), 3.04 (s, 3H), 2.52 (s, 3H); MS (ESI) m/e 364 (C21H21N3O3+H)+.

Workup

  1. temperaturecooled in an ice bath
  2. filtrationThe resulting precipitate was collected by filtration
  3. customdried
  4. customtriturated with diethyl ether
  5. customto yield a pale yellow solid
  6. customto precipitate an orange solid
  7. filtrationThe precipitated solid was collected by filtration
  8. customdried
  9. customtriturated with diethyl ether

Sources & evidence

ORD record
ord-09a64d4e3d224fa2bbe560e9aade43f3
Source dataset
uspto-grants-2013_05
Patent number
US08450307B2

Reaction notes

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