Hydrochloric Acid → HCID 59415756, compound

HRID 2061881Notes

Reaction equation

[CH2:1]([NH:3][C:4](=[O:24])[NH:5][C:6]1[N:11]=[CH:10][C:9](B(O)O)=[C:8]([C:15]2[S:16][CH:17]=[C:18]([C:20]([F:23])([F:22])[F:21])[N:19]=2)[CH:7]=1)[CH3:2].C(NC(NC1C=C(C2SC=C(C(F)(F)F)N=2)C(B2OC(C)(C)C(C)(C)O2)=CN=1)=O)C.[F:55][C:56]1[CH:64]=[CH:63][C:62](I)=[CH:61][C:57]=1[C:58]([OH:60])=[O:59].C(=O)([O-])[O-].[Cs+].[Cs+].Cl>O1CCOCC1.O.CCOC(C)=O>[CH2:1]([NH:3][C:4](=[O:24])[NH:5][C:6]1[N:11]=[CH:10][C:9]([C:62]2[CH:63]=[CH:64][C:56]([F:55])=[C:57]([CH:61]=2)[C:58]([OH:60])=[O:59])=[C:8]([C:15]2[S:16][CH:17]=[C:18]([C:20]([F:23])([F:22])[F:21])[N:19]=2)[CH:7]=1)[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

6-(3-ethylureido)-4-(4-(trifluoromethyl)thiazol-2-yl)pyridin-3-ylboronic acid (Intermediate 17, 0.261 g, 0.72 mmol, Intermediate 17) and 2-fluoro-5-iodobenzoic acid (0.175 g, 0.66 mmol, aldrich) were combined in dioxane (1 ml). A solution of cesium carbonate (0.364 g, 1.12 mmol) in water (0.658 ml) was added followed by tetrakis(triphenylphosine)palladium(0) (0.076 g, 0.07 mmol, strem) and additional dioxane (2.63 ml). The flask was placed in an oil bath preheated to 100° C. and was heated for 1h., then cooled to 0° C. and 1 N HCl was added until the pH was ˜3. EtOAc (5 ml) was added and a solid crashed out and was collected by filtration and washed with EtOAc, then dried to give a grey solid 5-(6-(3-ethylureido)-4-(4-(trifluoromethyl)thiazol-2-yl)pyridin-3-yl)-2-fluorobenzoic acid (0.180 g, 60.2%).

Workup

customThe flask was placed in an oil bath
custompreheated to 100° C.
temperaturewas heated for 1h.
filtrationwas collected by filtration
washwashed with EtOAc
customdried

Sources & evidence

ORD record: ord-4264cf7a6a7e42d8ace2a649e5339d9d
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08283361B2

Reaction notes

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