Lithium iodide → HCID 86700187, compound

HRID 879377Notes

Reaction equation

[C:1]([O:5][C@@H:6]([C:12]1[C:38]([CH3:39])=[CH:37][C:15]2[N:16]=[C:17]([C:19]3[CH:24]=[CH:23][N:22]=[C:21]([C:25]4[CH:26]=[C:27]5[C:32](=[CH:33][CH:34]=4)[N:31]=[C:30]([NH:35][CH3:36])[CH:29]=[CH:28]5)[CH:20]=3)[S:18][C:14]=2[C:13]=1[C:40]1[CH:45]=[CH:44][C:43]([Cl:46])=[CH:42][CH:41]=1)[C:7]([O:9]CC)=[O:8])([CH3:4])([CH3:3])[CH3:2].[Li+].[I-]>N1C=CC=CC=1>[C:1]([O:5][C@@H:6]([C:12]1[C:38]([CH3:39])=[CH:37][C:15]2[N:16]=[C:17]([C:19]3[CH:24]=[CH:23][N:22]=[C:21]([C:25]4[CH:26]=[C:27]5[C:32](=[CH:33][CH:34]=4)[N:31]=[C:30]([NH:35][CH3:36])[CH:29]=[CH:28]5)[CH:20]=3)[S:18][C:14]=2[C:13]=1[C:40]1[CH:45]=[CH:44][C:43]([Cl:46])=[CH:42][CH:41]=1)[C:7]([OH:9])=[O:8])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 170 °C

Procedure

To a stirred solution of (S)-ethyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(2-(2-(methylamino)quinolin-6-yl)pyridin-4-yl)benzo[d]thiazol-6-yl)acetate (4.1 mg, 0.006 mmol)) in pyridine (0.4 mL) was added LiI (50 mg, excess). The reaction mixture was heating in a microwave at 170° C. for 90 min. The mixture was concentrated in vacuo and then purified by reverse phase HPLC, eluting by 0-100% acetonitrile in H2O with 0.1% TFA to give the desired product. LCMS-ESI+ (m/z): [M+H]+ calcd for C35H32ClN4O3S: 623.2; found: 623.2. 1H NMR (400 MHz, CD3OD) δ 8.82 (d, J=5.2 Hz, 1H), 8.60 (s, 1H), 8.57 (s, 1H), 8.53 (d, J=8.8 Hz, 1H), 8.34 (d, J=9.6 Hz, 1H), 8.22-7.20 (m, 3H), 7.70 (d, J=9.2 Hz, 1H), 7.61 (s, 3H), 7.07 (d, J=8.4 Hz, 1H), 5.28 (s, 1H), 3.24 (s, 3H), 2.64 (s, 3H), 0.98 (s, 9H).

Workup

concentrationThe mixture was concentrated in vacuo
custompurified by reverse phase HPLC
washeluting by 0-100% acetonitrile in H2O with 0.1% TFA

Sources & evidence

ORD record: ord-127e21f527f245acaa1feea7a91eaf1c
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08987250B2

Reaction notes

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