Dichloromethane → HCID 67458952, compound

HRID 383430Notes

Reaction equation

HRID 383430 reaction equation
CS(OCC#[C:8][C:9]1[CH:14]=[C:13]([CH3:15])[CH:12]=[CH:11][C:10]=1[NH:16][C:17]([CH:19]1[O:24][C:23]2[CH:25]=[CH:26][C:27]([O:29][C:30]([F:33])([F:32])[F:31])=[CH:28][C:22]=2[NH:21][CH2:20]1)=[O:18])(=O)=O.[CH3:34][CH2:35][N:36]([CH:40]([CH3:42])C)[CH:37](C)[CH3:38].N1CC[O:46]CC1.[Cl:49]CCl>>[ClH:49].[ClH:49].[CH3:15][C:13]1[CH:12]=[CH:11][C:10]([NH:16][C:17]([CH:19]2[O:24][C:23]3[CH:25]=[CH:26][C:27]([O:29][C:30]([F:32])([F:33])[F:31])=[CH:28][C:22]=3[NH:21][CH2:20]2)=[O:18])=[C:9]([C:8]#[C:34][CH2:35][N:36]2[CH2:40][CH2:42][O:46][CH2:38][CH2:37]2)[CH:14]=1

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 8083MorpholineHCID 81531DiisopropylethylamineHCID 86643094HCID 86643094, compound

Product 1

HCID 67458952HCID 67458952, compoundYield 22%

Procedure

To 3-(5-methyl-2-(6-(trifluoromethoxy)-3,4-dihydro-2H-benzo[b][1,4]oxazine-2-carboxamido)phenyl)prop-2-ynyl methanesulfonate (20 mg, 0.04 mmol) in dichloromethane (1 mL) and DIEA (0.1 mmol) was added morpholine (36 μL, 0.4 mmol). The mixture was stirred for 10 hrs at room temperature. The mixture was concentrated in vacuo and then taken up in methanol. Purification via HPLC (10-99% CH3CN/5 mM HCl) provided N-(4-methyl-2-(3-morpholinoprop-1-ynyl)phenyl)-6-(trifluoromethoxy)-3,4-dihydro-2H-benzo[b][1,4]oxazine-2-carboxamide bis-hydrochloride (5 mg, 22% yield). LC/MS m/z 476.5 [M+H]+.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customPurification via HPLC (10-99% CH3CN/5 mM HCl)

Sources & evidence

ORD record
ord-c3a0b70492a746ecad02584ad4b4e0be
Source dataset
uspto-grants-2013_02
Patent number
US08367660B2

Reaction notes

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