Potassium Carbonate → HCID 67773713, compound

HRID 2201075Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([NH:10][CH2:11][C@@H:12]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH2:13][O:14][CH3:15])[CH:5]=[CH:6][C:7]=1[C:8]#[N:9].Cl.[NH2:25][C:26]1[S:30][N:29]=[C:28]([CH3:31])[CH:27]=1.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.C([O-])([O-])=O.[K+].[K+]>CC([O-])=O.CC([O-])=O.[Pd+2]>[C:8]([C:7]1[CH:6]=[CH:5][C:4]([NH:10][CH2:11][C@@H:12]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH2:13][O:14][CH3:15])=[CH:3][C:2]=1[NH:25][C:26]1[S:30][N:29]=[C:28]([CH3:31])[CH:27]=1)#[N:9]

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of (R)-tert-butyl 1-(3-bromo-4-cyanophenylamino)-3-methoxypropan-2-ylcarbamate (150 mg, 0.39 mmol), 5-amino-3-methylisothiazole hydrochloride (76 mg, 0.51 mmol), BINAP (25 mg, 0.04 mmol), Pd(OAc)2 (18 mg, 0.08 mmol) and K2CO3 (188 mg, 1.37 mmol) p-dioxane (3 mL) was degassed with Ar, then was heated at 120° C. for 15 h. the mixture was filtered, filter cake was washed with EtOAc, and the filtrated was concentrated in vacuo to give (R)-tert-butyl 1-(4-cyano-3-(3-methylisothiazol-5-ylamino)phenylamino)-3-methoxypropan-2-ylcarbamate as crude oil.

Workup

customwas degassed with Ar
filtrationwas filtered
filtrationfilter cake
washwas washed with EtOAc
concentrationthe filtrated was concentrated in vacuo

Sources & evidence

ORD record: ord-4be91f9bec3d45d7b4c22863d017833c
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09359375B2

Reaction notes

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