Dichloromethane → HCID 67458952, compound

HRID 1465166Notes

Reaction equation

HRID 1465166 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-d69a3a97dcf74a1986e44e4935a25454
Source dataset
uspto-grants-2015_04
Patent number
US08999976B2

Reaction notes

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