Lithium iodide → (S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(2-(8-oxo-1,7-naphthyridin-7(8H)-yl)pyridin-4-yl)benzo[d]thiazol-6-yl)acetic acid

HRID 879367Notes

Reaction equation

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

Participants

Conditions

Temperature: 170 °C

Procedure

To a solution of (S)-ethyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(2-(8-oxo-1,7-naphthyridin-7(8H)-yl)pyridin-4-yl)benzo[d]thiazol-6-yl)acetate (7.9 mg, 0.012 mmol) in pyridine (0.6 mL) was added LiI (75 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 C33H28ClN4O4S: 611.2; found: 611.2. 1H NMR (400 MHz, CDCl3) δ 9.06 (d, J=2.8 Hz, 1H), 8.68 (d, J=5.2 Hz, 1H), 8.62 (s, 1H), 8.08 (d, J=8.0 Hz, 1H), 7.99-7.92 (m, 3H), 7.76-7.69 (m, 2H), 7.55-7.49 (m, 3H), 6.66 (d, J=7.6 Hz, 1H), 5.34 (s, 1H), 2.58 (s, 3H), 1.01 (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-a09802ac394846de8a6d6aea433b5251
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08987250B2

Reaction notes

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