Dichloromethane → HCID 67458952, compound

HRID 472001Notes

Reaction equation

HRID 472001 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-0f475f7ad70744bc91a736c47df1d3fc
Source dataset
uspto-grants-2014_01
Patent number
US08633189B2

Reaction notes

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