Dimethylformamide → HCID 86700295, compound

HRID 879480Notes

Reaction equation

[C:1]([O:5][C@@H:6]([C:12]1[C:30]([CH3:31])=[CH:29][C:15]2[N:16]=[C:17]([C:19]3[CH:20]=[C:21]4C(=[CH:26][CH:27]=3)N[C:23](=O)[CH2:22]4)[S:18][C:14]=2[C:13]=1[C:32]1[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][CH:33]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8])([CH3:4])([CH3:3])[CH3:2].[C:39]([O-])([O-])=O.[Cs+].[Cs+].IC.[CH3:47][N:48]([CH:50]=[O:51])[CH3:49]>CCOC(C)=O>[C:1]([O:5][C@@H:6]([C:12]1[C:30]([CH3:31])=[CH:29][C:15]2[N:16]=[C:17]([C:19]3[CH:20]=[C:21]4[C:47](=[CH:26][CH:27]=3)[N:48]([CH3:49])[C:50](=[O:51])[C:22]4([CH3:23])[CH3:39])[S:18][C:14]=2[C:13]=1[C:32]1[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][CH:33]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 50 °C

Procedure

A vial was charged with (S)-ethyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(2-oxoindolin-5-yl)benzo[d]thiazol-6-yl)acetate (45 mg, 82 μmol), Cs2CO3 (134 mg, 0.410 mmol), iodomethane (51 μL, 0.82 mmol), and DMF (500 μL). The reaction was warmed to 50° C. for 2 h. The reaction was diluted with EtOAc and washed with 5% w/v aq LiCl (3×). The organic phase was dried (Na2SO4), filtered, and concentrated, giving the product, which was immediately used in the next step. LCMS-ESI+: calc'd for C30H29ClN2O4S: 591.2, 593.2 (M+H+); Found: 591.3, 593.3 (M+H+). 1H NMR (400 MHz, CD3CN): δ 8.04-7.88 (m, 2H), 7.81 (s, 1H), 7.63-7.48 (m, 4H), 7.02 (d, J=8.1 Hz, 1H), 5.18 (s, 1H), 4.32-4.06 (m, 2H), 3.15 (s, 3H), 2.51 (s, 3H), 1.41 (s, 6H), 1.27-1.12 (m, 3H), 0.94 (s, 9H).

Workup

washwashed with 5% w/v aq LiCl (3×)
dry with materialThe organic phase was dried (Na2SO4)
filtrationfiltered
concentrationconcentrated
customgiving the product, which

Sources & evidence

ORD record: ord-fcfeac52e5e847f7b7721d7489687ed4
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08987250B2

Reaction notes

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