Glycine → HCID 57989962, compound

HRID 1961909Notes

Reaction equation

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

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of N-{3-[5-(2-chloro-4-pyrimidinyl)-2-(1-methylethyl)-1,3-thiazol-4-yl]phenyl}-3-fluorobenzenesulfonamide (100 mg, 0.20 mmol) in 1-butanol (5 mL) was added glycine (153 mg, 2.0 mmol) and K2CO3 (566 mg, 4.0 mmol). The reaction was stirred at 60° C. for 16 h, then partitioned between water and EtOAc. The pH of the aqueous layer was adjusted to below 4 with 1 N HCl, and the aqueous layer was extracted with EtOAc. This organic layer was dried over anhydrous Na2SO4, filtered, and concentrated to generate the title compound as a white powder (24 mg, 0.05 mmol, 22.8% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.04 (d, J=4.5 Hz, 1H), 7.46-7.64 (m, 5H), 7.33 (t, J=8.1 Hz, 1H), 7.18-7.24 (m, 3H), 6.07 (s, 1H), 3.89 (s, 2H), 3.25-3.29 (m, 1H), 1.36 (d, J=6.7 Hz, 6H). MS (ESI): 528.1 [M+H]+.

Workup

custompartitioned between water and EtOAc
extractionthe aqueous layer was extracted with EtOAc
dry with materialThis organic layer was dried over anhydrous Na2SO4
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-847e2637058245428baca4d99015caba
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08415345B2

Reaction notes

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