Phenyl chloroformate → HCID 178488703, 화합물

HRID 968539

반응식

HRID 968539 반응식
[CH3:1][O:2][C:3]1[C:8]2[N:9]=[C:10]([NH2:12])[S:11][C:7]=2[C:6]([CH:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)=[CH:5][CH:4]=1.Cl[C:20]([O:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:21].C([O:36]C(=O)NC1SC2C(C3C=CC=CC=3)=CC=C(OC)C=2N=1)C1C=CC=CC=1.C(N(C(C)C)C(C)C)C.[C@H]1(O)CC[C@H](O)CC1>CS(C)=O.ClCCl>[OH:36][C@H:26]1[CH2:27][CH2:28][C@H:23]([O:22][C:20](=[O:21])[NH:12][C:10]2[S:11][C:7]3[C:6]([CH:13]4[CH2:18][CH2:17][O:16][CH2:15][CH2:14]4)=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[C:8]=3[N:9]=2)[CH2:24][CH2:25]1

참가 물질

8

반응물 5

HCID 15891Phenyl chloroformateHCID 81531DiisopropylethylamineHCID 220157354-Methoxy-7-(tetrahydro-pyran-4-yl)-benzothiazol-2-yl-amineHCID 86584926(4-Methoxy-7-phenyl-benzothiazol-2-yl)-carbamic acid benzyl esterHCID 178521615HCID 178521615, 화합물

생성물 1

HCID 178488703HCID 178488703, 화합물수율 7%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 6344Dichloromethane용매

실험 절차

4-Methoxy-7-(tetrahydro-pyran-4-yl)-benzothiazol-2-ylamine (69 mg, 0.26 mmol) is 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 N-ethyl-diisopropylamine (0.090 ml, 0.52 mmol) and (trans)-cyclohexane-1,4-diol (60 mg, 0.52 mmol) in dimethyl sulfoxide (10 ml) at 50° C. for 2 h. Then 100 ml dichoromethane are added, the mixture is extracted with saturated aqueous sodium carbonate and the organic phase is dried and evaporated. Flash-chromatographic purification (silica, eluting with dichloromethane/methanol) yielded the title compound as white solid (7% yield). MS: m/e=407(M+H+), mp 282-284° C. Following the general method of example 1 the compounds of examples 2 to 11 were prepared.

후처리

  1. extractionthe mixture is extracted with saturated aqueous sodium carbonate
  2. customthe organic phase is dried
  3. customevaporated
  4. customFlash-chromatographic purification (silica, eluting with dichloromethane/methanol)

출처 및 근거

ORD 기록
ord-11fd3b0b8d58482a8356e58c8abe301d
출처 데이터셋
uspto-grants-2007_12
특허 번호
US07304058B2

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