Hydrochloric Acid → HCID 10628651, compound

HRID 1422062Notes

Reaction equation

HRID 1422062 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C:12]1[C:17](=[O:18])[N:16]([CH2:19][C:20]([NH:22][CH:23]([CH:31]([C:33]2[O:34][C:35]3[CH:41]=[CH:40][C:39]([C:42](O)=[O:43])=[CH:38][C:36]=3[N:37]=2)[OH:32])[CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:21])[C:15]([C:45]2[CH:50]=[CH:49][C:48]([F:51])=[CH:47][CH:46]=2)=[N:14][CH:13]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[CH2:53]([NH2:55])[CH3:54].C1C=CC2N(O)N=NC=2C=1.C(N1CCOCC1)C.CCN=C=NCCCN(C)C.Cl.Cl>CN(C=O)C>[CH2:1]([O:8][C:9]([NH:11][C:12]1[C:17](=[O:18])[N:16]([CH2:19][C:20]([NH:22][CH:23]([CH:31]([C:33]2[O:34][C:35]3[CH:41]=[CH:40][C:39]([C:42]([NH:55][CH2:53][CH3:54])=[O:43])=[CH:38][C:36]=3[N:37]=2)[OH:32])[CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:21])[C:15]([C:45]2[CH:50]=[CH:49][C:48]([F:51])=[CH:47][CH:46]=2)=[N:14][CH:13]=1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 7525EthylmorpholineHCID 11198Ethylamine hydrochlorideHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 10652239HCID 10652239, compound

Product 1

HCID 10628651HCID 10628651, compoundYield 84,848.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of the objective compound (450 mg, 0.651 mmol) of Step (1), ethylamine hydrochloride (67 mg, 0.82 mmol) and HOBT (176 mg, 1.30 mmol) in DMF (10 mL) were added N-ethylmorpholine (0.10 mL, 0.79 mmol) and WSCI hydrochloride (148 mg, 0.772 mmol) and the mixture was stirred at room temperature for 3.5 hours. The reaction mixture was added to 1N hydrochloric acid (80 mL) and extracted with ethyl acetate. The extract was washed successively with a saturated aqueous sodium hydrogencarbonate solution and saturated brine, dried over magnesium sulfate and concentrated under reduced pressure. The obtained solid was washed with ether and dried in vacuo to give 2-[5-benzyloxycarbonylamino-2-(4-fluorophenyl)-6-oxo-1,6-dihydro-1-pyrimidinyl]-N-[1-[[5-(ethylaminocarbonyl)benzoxazol-2-yl]hydroxymethyl]-2-phenylethyl]acetamide as a white solid (397 g, 85%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed successively with a saturated aqueous sodium hydrogencarbonate solution and saturated brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. washThe obtained solid was washed with ether
  6. customdried in vacuo

Sources & evidence

ORD record
ord-ba4a4d0d74304be6a681d6f09ab72224
Source dataset
uspto-grants-2000_06
Patent number
US06080738

Reaction notes

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