Methanol → HCID 11978199, compound

HRID 132257Notes

Reaction equation

HRID 132257 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[CH2:11][CH:10]([NH:12][C:13]([N:15]3[CH2:20][CH2:19][CH:18]([N:21]4[CH2:30][C:29]5[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=5)[NH:23][C:22]4=[O:31])[CH2:17][CH2:16]3)=[O:14])[C:9](=[O:32])[N:8]([CH3:33])[CH2:7][C:6]=2C=1.CO.CCOCC.S(Cl)([Cl:45])(=O)=O.Cl[CH2:48][Cl:49]>>[Cl:45][C:3]1[C:2]([OH:1])=[C:48]([Cl:49])[C:6]2[CH2:7][N:8]([CH3:33])[C:9](=[O:32])[CH:10]([NH:12][C:13]([N:15]3[CH2:20][CH2:19][CH:18]([N:21]4[CH2:30][C:29]5[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=5)[NH:23][C:22]4=[O:31])[CH2:17][CH2:16]3)=[O:14])[CH2:11][C:5]=2[CH:4]=1

Participants

6

Reactant 5

HCID 887MethanolHCID 3283Diethyl EtherHCID 6344DichloromethaneHCID 24648Sulfuryl chlorideHCID 11978198HCID 11978198, compound

Product 1

HCID 11978199HCID 11978199, compoundYield 58%

Procedure

To a stirred solution of 4-(2-oxo-1,4-dihydro-2H-quinazolin-3-yl)-piperidine-1-carboxylic acid (8-hydroxy-2-methyl-3-oxo-2,3,4,5-tetrahydro-1H-benzo[c]azepin-4-yl)-amide (27 mg, 0.058 mmol) in dichloromethane (10 mL) was added methanol (2 mL), ether (3 mL) followed by sulfuryl chloride (70 μL) at room temperature. The reaction mixture was stirred for additional 12 h and then concentrated. The crude product was purified by Prep HPLC to give 4-(2-Oxo-1,4-dihydro-2H-quinazolin-3-yl)-piperidine-1-carboxylic acid (7,9-dichloro-8-hydroxy-2-methyl-3-oxo-2,3,4,5-tetrahydro-1H-benzo[c]azepin-4-yl)-amide in 58% yield. MS (ESI) 532 (M+H); Rf=1.40.

Workup

  1. concentrationconcentrated
  2. customThe crude product was purified by Prep HPLC

Sources & evidence

ORD record
ord-740a31c81ad44d97af44d1fa57dd5daa
Source dataset
uspto-grants-2008_06
Patent number
US07384930B2

Reaction notes

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