4-Methylmorpholine → HCID 59331442, compound

HRID 1881988Notes

Reaction equation

HRID 1881988 reaction equation
Cl.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1.CN1CC[O:27][CH2:26][CH2:25]1.[CH:30]1([S:33]([C:36]2[CH:41]=[CH:40][C:39]([CH:42]([C:50]3[NH:54][C:53]([C:55]4[N:60]=[CH:59][C:58]([CH2:61][N:62]5[CH2:67][CH2:66][NH:65][C@@H:64]([CH3:68])[CH2:63]5)=[CH:57][CH:56]=4)=[CH:52][CH:51]=3)[CH2:43][CH:44]3[CH2:49][CH2:48][O:47][CH2:46][CH2:45]3)=[CH:38][CH:37]=2)(=[O:35])=[O:34])[CH2:32][CH2:31]1>O1CCCC1.C(OCC)(=O)C.C(O)(=O)C>[C:26]([N:65]1[CH2:66][CH2:67][N:62]([CH2:61][C:58]2[CH:59]=[N:60][C:55]([C:53]3[NH:54][C:50]([CH:42]([C:39]4[CH:38]=[CH:37][C:36]([S:33]([CH:30]5[CH2:32][CH2:31]5)(=[O:34])=[O:35])=[CH:41][CH:40]=4)[CH2:43][CH:44]4[CH2:45][CH2:46][O:47][CH2:48][CH2:49]4)=[CH:51][CH:52]=3)=[CH:56][CH:57]=2)[CH2:63][C@@H:64]1[CH3:68])(=[O:27])[CH3:25]

Participants

8

Reactant 4

HCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 59331341HCID 59331341, compound

Product 1

HCID 59331442HCID 59331442, compoundYield 90%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of acetic acid (5.6 μL) in tetrahydrofuran (2 mL) were added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (25.0 mg), 1-hydroxybenzotriazole (18.0 mg) and N-methylmorpholine (30 μL), and the mixture was stirred at room temperature for 30 min. To to the reaction mixture was added a solution of (3S)-1-{[6-(5-{1-[4-(cyclopropylsulfonyl)phenyl]-2-(tetrahydro-2H-pyran-4-yl)ethyl}-1H-pyrrol-2-yl)pyridin-3-yl]methyl}-3-methylpiperazine (45.0 mg) in tetrahydrofuran (1 mL), and the mixture was stirred overnight at room temperature. The reaction mixture was diluted with ethyl acetate, washed with water and saturated brine, dried (MgSO4) and concentrated. The residue was subjected to basic silica gel column chromatography, and the title compound (43.0 mg, yield 90%) was obtained as a pale-yellow amorphous solid from a fraction eluted with ethyl acetate. MS: 591 (MH+).

Workup

  1. stirringthe mixture was stirred overnight at room temperature
  2. washwashed with water and saturated brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-7db68c0cdf5542b59ec8f7dd8197c451
Source dataset
uspto-grants-2012_11
Patent number
US08318746B2

Reaction notes

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