1,2-Dichloroethane → HCID 86668065, compound

HRID 538354Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[C:4]([C:9]2([CH2:16][F:17])[NH:14][C:13](=[S:15])[CH2:12][O:11][CH2:10]2)[C:5]([Cl:8])=[N:6][CH:7]=1.[Br:18][C:19]1[CH:20]=[CH:21][C:22]([C:25](O)=[O:26])=[N:23][CH:24]=1.C1C=NC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.C(Cl)CCl>CN(C=O)C>[Cl:8][C:5]1[N:6]=[CH:7][C:2]([NH:1][C:25]([C:22]2[CH:21]=[CH:20][C:19]([Br:18])=[CH:24][N:23]=2)=[O:26])=[CH:3][C:4]=1[C:9]1([CH2:16][F:17])[CH2:10][O:11][CH2:12][C:13](=[S:15])[NH:14]1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 5-(5-amino-2-chloro-pyridin-3-yl)-5-fluoromethyl-morpholine-3-thione (33 mg, 0.12 mmol), 5-bromo-pyridine-2-carboxylic acid (36 mg, 0.18 mmol) and HOAt (29 mg, 0.215 mmol) in DMF (0.4 ml) was cooled to 0° C. and DIPEA (0.042 ml, 0.24 mmol) and EDC (34 mg, 0.18 mmol) were added, the reaction mixture was stirred at 0° C. for 10 min, then allowed to warm to room temperature over night. At 0° C. aq. 1M KHCO3 was added and the mixture extracted with toluene. The combined organic layers were washed with water, dried with Na2SO4 and evaporated. The residue was taken up in DCM/MeOH 65/35 from which the product started to crystallize. Filtration, rinsing of the crystallized material with DCM and drying provide the title compound as yellow crystals.

Workup

temperatureto warm to room temperature over night
extractionthe mixture extracted with toluene
washThe combined organic layers were washed with water
dry with materialdried with Na2SO4
customevaporated
customto crystallize
filtrationFiltration
washrinsing of the crystallized material with DCM
customdrying

Sources & evidence

ORD record: ord-c9f58d0c786c4d1bb5bf9ab5c0f35492
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08865712B2

Reaction notes

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