Sodium Carbonate → HCID 57642327, compound

HRID 2112492Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:14]2[CH:15]=[C:16]([C:20]#[N:21])[C:17]([OH:19])=[CH:18][C:13]=2[NH:12][C:11](=[O:22])[CH2:10][N:9]=1.C(=O)([O-])[O-].[Na+].[Na+].Cl[CH2:30][CH2:31][CH2:32][N:33]1[CH2:38][CH2:37][O:36][CH2:35][CH2:34]1>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:14]2[CH:15]=[C:16]([C:20]#[N:21])[C:17]([O:19][CH2:30][CH2:31][CH2:32][N:33]3[CH2:38][CH2:37][O:36][CH2:35][CH2:34]3)=[CH:18][C:13]=2[NH:12][C:11](=[O:22])[CH2:10][N:9]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 0.322 g (0.00103 mole) of 5-(2-chlorophenyl)-7-cyano-1,3-dihydro-8-hydroxy-2H-1,4-benzodiazepin-2-one (Iqq), 6 mL of dimethylformamide, 0.132 g (0.00124 mole) of sodium carbonate and 0.2028 g (0.00124 mole) of 4-(3-chloropropyl)-morpholine was stirred 50° C. under an atmosphere of argon for 24 hours. The mixture was then cooled and partitioned between ethyl acetate and water. The aqueous phase was reextracted with ethyl acetate and the ethyl acetate extracts were then dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by chromatography on silica gel eluting with acetonitrile-methanol (90:10), to provide 0.199 g of 5-(2-chlorophenyl)-7-cyano-1,3-dihydro-8-(3-(4-morpholinyl)propoxy)-2H-1,4-benzodiazepin-2-one (Ik). MH+/Z=439.

Workup

temperatureThe mixture was then cooled
custompartitioned between ethyl acetate and water
dry with materialthe ethyl acetate extracts were then dried over anhydrous sodium sulfate
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe residue was purified by chromatography on silica gel eluting with acetonitrile-methanol (90:10)

Sources & evidence

ORD record: ord-6bd1ae83c0ab4bf9bc03923bca93090b
Source dataset: uspto-grants-2009_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07524840B2

Reaction notes

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