1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → N-(2-(tert-butyldiphenylsilyloxy)ethyl)-8-(1-(3,5-difluorophenylamino)ethyl)-N-methyl-2-morpholino-4-oxo-4H-chromene-6-carboxamide

HRID 572790Notes

Reaction equation

HRID 572790 reaction equation
Cl.CN(C)CCCN=C=NCC.[F:13][C:14]1[CH:15]=[C:16]([NH:21][CH:22]([C:24]2[CH:25]=[C:26]([C:41](O)=[O:42])[CH:27]=[C:28]3[C:33]=2[O:32][C:31]([N:34]2[CH2:39][CH2:38][O:37][CH2:36][CH2:35]2)=[CH:30][C:29]3=[O:40])[CH3:23])[CH:17]=[C:18]([F:20])[CH:19]=1.[Si:44]([O:61][CH2:62][CH2:63][NH:64][CH3:65])([C:57]([CH3:60])([CH3:59])[CH3:58])([C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1)[C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1.OC1C=CC=C[N+]=1[O-]>C(Cl)Cl>[Si:44]([O:61][CH2:62][CH2:63][N:64]([CH3:65])[C:41]([C:26]1[CH:27]=[C:28]2[C:33](=[C:24]([CH:22]([NH:21][C:16]3[CH:17]=[C:18]([F:20])[CH:19]=[C:14]([F:13])[CH:15]=3)[CH3:23])[CH:25]=1)[O:32][C:31]([N:34]1[CH2:39][CH2:38][O:37][CH2:36][CH2:35]1)=[CH:30][C:29]2=[O:40])=[O:42])([C:57]([CH3:59])([CH3:60])[CH3:58])([C:51]1[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=1)[C:45]1[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=1

Participants

6

Reactant 4

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 118231582-(tert-butyldiphenylsilyloxy)-N-methylethanamineHCID 582349718-(1-(3,5-difluorophenylamino)ethyl)-2-morpholino-4-oxo-4H-chromene-6-carboxylic acidHCID 178526252HCID 178526252, compound

Product 1

HCID 67103917N-(2-(tert-butyldiphenylsilyloxy)ethyl)-8-(1-(3,5-difluorophenylamino)ethyl)-N-methyl-2-morpholino-4-oxo-4H-chromene-6-carboxamideYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (135 mg, 0.71 mmol) was added in one portion to 8-(1-(3,5-difluorophenylamino)ethyl)-2-morpholino-4-oxo-4H-chromene-6-carboxylic acid (200 mg, 0.35 mmol, enantiomer 1; [α]D20°: +115°), 2-(tert-butyldiphenylsilyloxy)-N-methylethanamine (221 mg, 0.71 mmol) and 2-hydroxy-pyridine N-oxide (78 mg, 0.71 mmol) dissolved in DCM (2 mL) under argon. The resulting solution was stirred at RT overnight. The solution was evaporated to dryness, water was added and product was extracted with DCM. The organic phase was washed with brine and dried over magnesium sulfate, the solvent was evaporated to afford N-(2-(tert-butyldiphenylsilyloxy)ethyl)-8-(1-(3,5-difluorophenylamino)ethyl)-N-methyl-2-morpholino-4-oxo-4H-chromene-6-carboxamide (94%) as a white solid. Mass Spectrum: M+H+ 726.

Workup

  1. customThe solution was evaporated to dryness, water
  2. additionwas added
  3. extractionproduct was extracted with DCM
  4. washThe organic phase was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. customthe solvent was evaporated

Sources & evidence

ORD record
ord-c9a0842ed0eb45f0af9aa9e9311b79fe
Source dataset
uspto-grants-2015_05
Patent number
US09029374B2

Reaction notes

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