Diisopropylethylamine → 1-ethyl-3-[7-[(E)-methoxyiminomethyl]-5-phenylmethoxy-1,3-benzothiazol-2-yl]urea

HRID 712270Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:24]=O)[C:12]2[S:16][C:15]([NH:17][C:18]([NH:20][CH2:21][CH3:22])=[O:19])=[N:14][C:13]=2[CH:23]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[O:27]([NH2:29])[CH3:28].CCN(C(C)C)C(C)C>CN(C=O)C>[CH2:1]([O:8][C:9]1[CH:10]=[C:11](/[CH:24]=[N:29]/[O:27][CH3:28])[C:12]2[S:16][C:15]([NH:17][C:18]([NH:20][CH2:21][CH3:22])=[O:19])=[N:14][C:13]=2[CH:23]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 105 °C

Procedure

1-(5-(Benzyloxy)-7-formylbenzo[d]thiazol-2-yl)-3-ethylurea (425 mg, 1.20 mmol), methoxylamine hydrochloride (105.2 mg, 1.26 mmol) and N,N′-diisopropylethylamine (0.77 g, 1.05 ml) were stirred in DMF degassed with N2. The reaction was purged with N2, sealed and heated to 105° C. for 18 h. LCMS after indicated complete consumption of starting material. The solvents were removed under reduced pressure and the resulting residue absorbed onto silica and purified by flash column chromatography eluting with 0 to 100% EtOAc in petroleum-ether to afford the product as a white solid 325 mg (70%) which was used directly in the next step.

Workup

customdegassed with N2
customThe reaction was purged with N2
customsealed
customconsumption of starting material
customThe solvents were removed under reduced pressure
customthe resulting residue absorbed onto silica
custompurified by flash column chromatography
washeluting with 0 to 100% EtOAc in petroleum-ether

Sources & evidence

ORD record: ord-d935f1f5aa3b4f52b253ee7bb57d237a
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181234B2

Reaction notes

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