HCID 68509346, compound → HCID 46911539, compound

HRID 12635Notes

Reaction equation

HRID 12635 reaction equation
[NH2:1][C:2]([C:4]1[C:12]2[N:11]=[C:10]([C:13]3([NH:29]C(OCC4C5C=CC=CC=5C5C4=CC=CC=5)=O)[CH2:18][CH2:17][N:16]([C:19]([O:21][CH2:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)=[O:20])[CH2:15][CH2:14]3)[NH:9][C:8]=2[CH:7]=[CH:6][CH:5]=1)=[O:3]>CN(C=O)C.N1CCCCC1>[NH2:29][C:13]1([C:10]2[NH:9][C:8]3[CH:7]=[CH:6][CH:5]=[C:4]([C:2]([NH2:1])=[O:3])[C:12]=3[N:11]=2)[CH2:18][CH2:17][N:16]([C:19]([O:21][CH2:22][C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)=[O:20])[CH2:15][CH2:14]1

Participants

4

Reactant 1

HCID 68509346HCID 68509346, compound

Product 1

HCID 46911539HCID 46911539, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8082PiperidineSolvent

Procedure

A mixture of Example 49A (0.035 g, 0.1 mmol) in DMF (2 ml) and piperidine (0.5 ml), was stirred at room temperature for 2 h. The mixture was concentrated under vacuum then crystallized from MeOH to provide 0.014 g (64%) of the desired product. MS (ESI) m/e 416 (M+Na)+. 1H NMR (DMSO-D6) δ ppm 8.14 (s, 1H), 7.84 (d, J=7.02 Hz 1H), 7.73 (s, 2H) 7.37-7.40 (m, 4H), 7.31-7.37 (m, 2H), 5.11 (s, 2H), 3.51-3.68 (m, 6H), 2.32 (s, 2H), 1.88 (d, J=13.43 Hz, 2H).

Workup

  1. concentrationThe mixture was concentrated under vacuum
  2. customthen crystallized from MeOH

Sources & evidence

ORD record
ord-0e6f6c0cbc074aa498a506bae30807b8
Source dataset
uspto-grants-2010_06
Patent number
US07728026B2

Reaction notes

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