Sodium hydride → HCID 59809539, compound

HRID 2114487Notes

Reaction equation

HRID 2114487 reaction equation
[H-].[Na+].[C:3]([O:7][C:8]([N:10]1[CH2:15][CH2:14][CH:13]([NH:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]#[N:24])=[CH:19][C:18]=2[O:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2Br)[CH2:12][CH2:11]1)=[O:9])([CH3:6])([CH3:5])[CH3:4]>CN(C=O)C>[C:3]([O:7][C:8]([N:10]1[CH2:15][CH2:14][CH:13]([N:16]2[C:17]3[CH:22]=[CH:21][C:20]([C:23]#[N:24])=[CH:19][C:18]=3[O:25][C:26]3[C:31]2=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH2:12][CH2:11]1)=[O:9])([CH3:6])([CH3:5])[CH3:4]

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 59809564HCID 59809564, compound2×

Product 1

HCID 59809539HCID 59809539, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
120 °C

Procedure

To a suspension of sodium hydride (0.1-1 g; 0.74 mmol) in DMF (5 mL) was added a solution of 4-[2-(2-bromophenoxy)-4-cyanophenylamino]-piperidine-1-carboxylic acid tert-butyl ester, 3a (0.35 g; 0.74 mmol) in DMF (3 mL). The mixture was heated to 120° C. for 90 min and allowed to cool to rt. The mixture was poured into ice-water and a precipitate formed. The solid was separated via filtration, dried to yield 4-(3-cyanophenoxazin-10-yl)-piperidine-1-carboxylic acid tert-butyl ester, 4a. MS m/z (M+Na) 413.9. The material was used as such for the next reaction.

Workup

  1. temperatureto cool to rt
  2. customa precipitate formed
  3. customThe solid was separated via filtration
  4. customdried

Sources & evidence

ORD record
ord-657dbedd513e47ed938e84303ac7bbb5
Source dataset
uspto-grants-2008_10
Patent number
US07432257B2

Reaction notes

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