Morpholine → Morpholine-4-carboxylic acid (7-[1,4]dioxepan-6-yl-4-methoxy-benzothiazol-2-yl)-amide

HRID 2222138Notes

Reaction equation

[O:1]1[CH2:7][CH:6]([C:8]2[C:16]3[S:15][C:14]([NH2:17])=[N:13][C:12]=3[C:11]([O:18][CH3:19])=[CH:10][CH:9]=2)[CH2:5][O:4][CH2:3][CH2:2]1.Cl[C:21]([O:23][C:24]1[CH:29]=CC=CC=1)=O.C([O:37][C:38](=O)[NH:39][C:40]1SC2C(C3C=CC=CC=3)=CC=C(OC)C=2N=1)C1C=CC=CC=1.N1CCOCC1>>[O:4]1[CH2:5][CH:6]([C:8]2[C:16]3[S:15][C:14]([NH:17][C:38]([N:39]4[CH2:40][CH2:21][O:23][CH2:24][CH2:29]4)=[O:37])=[N:13][C:12]=3[C:11]([O:18][CH3:19])=[CH:10][CH:9]=2)[CH2:7][O:1][CH2:2][CH2:3]1

Participants

Reactant 4

HCID 8083Morpholine

HCID 15891Phenyl chloroformate

HCID 597118057-[1,4]Dioxepan-6-yl-4-methoxy-benzothiazol-2-ylamine

HCID 86584926(4-Methoxy-7-phenyl-benzothiazol-2-yl)-carbamic acid benzyl ester

Product 1

HCID 11326842Morpholine-4-carboxylic acid (7-[1,4]dioxepan-6-yl-4-methoxy-benzothiazol-2-yl)-amide

Procedure

7-[1,4]Dioxepan-6-yl-4-methoxy-benzothiazol-2-ylamine was first reacted with phenyl chloroformate as described for (4-methoxy-7-phenyl-benzothiazol-2-yl)-carbamic acid benzyl ester in WO01/97786 and then with morpholine. Usual workup, peparative reversed-phase HPLC and final dry-freezing afforded the title compound as light brown powder. MS: m/e=394(M+H+).

Workup

customUsual workup, peparative reversed-phase HPLC and final dry-freezing

Sources & evidence

ORD record: ord-dfda485f9e2c490986edb32e52098f60
Source dataset: uspto-grants-2008_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07371748B2

Reaction notes

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