6-(3-Chloro-thiophen-2-yl)-2,2-dimethyl-[1,3]dioxin-4-one → {4-(6-Benzyloxy-pyridin-3-yl)-2-[3-(3-chloro-thiophen-2-yl)-3-oxo-propionylamino]-phenyl}-carbamic acid tert.-butyl ester

HRID 859406Notes

Reaction equation

HRID 859406 reaction equation
[C:1]([O:5][C:6](=[O:29])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:15]=[N:16][C:17]([O:20][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[CH:18][CH:19]=2)=[CH:10][C:9]=1[NH2:28])([CH3:4])([CH3:3])[CH3:2].[Cl:30][C:31]1[CH:35]=[CH:34][S:33][C:32]=1[C:36]1[O:41]C(C)(C)[O:39][C:38](=O)[CH:37]=1>>[C:1]([O:5][C:6](=[O:29])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:15]=[N:16][C:17]([O:20][CH2:21][C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)=[CH:18][CH:19]=2)=[CH:10][C:9]=1[NH:28][C:38](=[O:39])[CH2:37][C:36]([C:32]1[S:33][CH:34]=[CH:35][C:31]=1[Cl:30])=[O:41])([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 222247756-(3-Chloro-thiophen-2-yl)-2,2-dimethyl-[1,3]dioxin-4-oneHCID 69592766Carbamic acid,[2-amino-4-[6-(phenylmethoxy)-3-pyridinyl]phenyl]-,1,1-dimethylethyl ester

Product 1

HCID 86588014{4-(6-Benzyloxy-pyridin-3-yl)-2-[3-(3-chloro-thiophen-2-yl)-3-oxo-propionylamino]-phenyl}-carbamic acid tert.-butyl esterYield 54.1%

Procedure

Prepared from [2-amino-4-(6-benzyloxy-pyridin-3-yl)-phenyl]-carbamic acid tert.-butyl ester (Example G30) (216 mg, 0.55 mmol) and 6-(3-chloro-thiophen-2-yl)-2,2-dimethyl-[1,3]dioxin-4-one (Example J2) (142 mg, 0.58 mmol) according to the general procedure K. Obtained as a beige solid (172 mg).

Sources & evidence

ORD record
ord-6a893efbaa2b4d44afcf9c4453f1ed89
Source dataset
uspto-grants-2006_12
Patent number
US07151098B2

Reaction notes

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