Piperidine → HCID 22625855, compound

HRID 277857Notes

Reaction equation

HRID 277857 reaction equation
[C:1]([C:3]1[N:7]([CH3:8])[C:6]([C:9]2[CH:10]=[CH:11][C:12]3[N:17](C(OCC4C5C=CC=CC=5C5C4=CC=CC=5)=O)[CH:16]([CH3:35])[O:15][C:14]([CH3:37])([CH3:36])[C:13]=3[CH:38]=2)=[CH:5][CH:4]=1)#[N:2].N1CCCCC1>CN(C=O)C>[CH3:8][N:7]1[C:6]([C:9]2[CH:10]=[CH:11][C:12]3[NH:17][CH:16]([CH3:35])[O:15][C:14]([CH3:37])([CH3:36])[C:13]=3[CH:38]=2)=[CH:5][CH:4]=[C:3]1[C:1]#[N:2]

Participants

4

Reactant 2

HCID 8082PiperidineHCID 23435575HCID 23435575, compound

Product 1

HCID 22625855HCID 22625855, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Prepared according to the procedure for Example 20 from 9H-fluoren-9-ylmethyl 6-(5-cyano-1-methyl-1H-pyrrol-2-yl)-2,4,4-trimethyl-2H-3,1-benzoxazine-1(4H)-carboxylate (0.3 g, 0.6 mmol) and 20% piperidine in DMF. A white solid (0.07 g, 42%): mp 195-196° C.; 1H-NMR (DMSO-d6) δ 7.16 (d, 1H, J=2.8 Hz), 7.08 (dd, 1H, J=8.1, 1.9 Hz), 6.98 (d, 1H, J=4.1 Hz), 6.63 (d, 1H, J=8.5 Hz), 6.61 (s, 1H), 6.20 (d, 1H, J=4.1 Hz), 4.79-4.81 (m, 1H), 3.67 (s, 3H), 1.49 (s, 3H), 1.27 (d, 3H, J=5.5 Hz); MS (ESI) m/z 282 [M+H]+.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-06222a2c7a464dcaa2459af59a873f1b
Source dataset
uspto-grants-2002_03
Patent number
US06358948B1

Reaction notes

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