1,2-Dichloroethane → HCID 89495512, compound
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]([CH3:14])([CH3:13])[C:10]([OH:12])=O)[CH:5]=[N:6][CH:7]=1.[F:15][C:16]([F:20])([F:19])[CH2:17][NH2:18].C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.C(Cl)CCl>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]([CH3:14])([CH3:13])[C:10]([NH:18][CH2:17][C:16]([F:20])([F:19])[F:15])=[O:12])[CH:5]=[N:6][CH:7]=1Participants
Procedure
To a mixture of 2-[(5-bromopyridin-3-yl)amino]-2-methylpropanoic acid I-4b (2.0 g, 7.72 mmol), 2,2,2-trifluoroethylamine (1.214 mL, 15.44 mmol), HOBT (1.773 g, 11.58 mmol) and DIPEA (2.70 mL, 15.44 mmol) in DMF (20 mL) was added EDC (2.220 g, 11.58 mmol). The mixture was allowed to stir at RT for 18 hr. The reaction was quenched into water (100 mL) and ethyl acetate (100 mL) and aq. KHSO4 added to adjust the pH to 6.5. Organic layer removed, washed with aqueous NaHCO3 (50 mL) and then brine (50 mL). The aqueous extracts were washed with ethyl acetate (50 mL). Organics combined, dried over sodium sulfate, filtered thru a pad of silica and concentrated to give a solid 2.9 gms. Solid slurried in ether, sonicated and filtered to give 2.4 g, (91%) title compound, I-4, as a white solid.
Workup
- customThe reaction was quenched into water (100 mL) and ethyl acetate (100 mL) and aq. KHSO4
- additionadded
- customOrganic layer removed
- washwashed with aqueous NaHCO3 (50 mL)
- washThe aqueous extracts were washed with ethyl acetate (50 mL)
- dry with materialdried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-ae03335f36964041b009c830739f6c0f
- Source dataset
- uspto-grants-2015_08
- Patent number
- US09096598B2
Reaction notes
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