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

HRID 879383Notes

Reaction equation

[C:1]([O:5][C@@H:6]([C:12]1[C:31]([CH3:32])=[CH:30][C:15]2[N:16]=[C:17]([N:19]3[CH:28]=[CH:27][C:26]4[C:21](=[CH:22][N:23]=[CH:24][CH:25]=4)[C:20]3=[O:29])[S:18][C:14]=2[C:13]=1[C:33]1[CH:38]=[CH:37][C:36]([Cl:39])=[CH:35][CH:34]=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:31]([CH3:32])=[CH:30][C:15]2[N:16]=[C:17]([N:19]3[CH:28]=[CH:27][C:26]4[C:21](=[CH:22][N:23]=[CH:24][CH:25]=4)[C:20]3=[O:29])[S:18][C:14]=2[C:13]=1[C:33]1[CH:38]=[CH:37][C:36]([Cl:39])=[CH:35][CH:34]=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-(1-oxo-2,7-naphthyridin-2(1H)-yl)benzo[d]thiazol-6-yl)acetate (18.8 mg, 0.034 mmol)) in pyridine (0.8 mL) was added LiI (100 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 C28H25ClN3O4S: 534.1; found: 534.2. 1H NMR (400 MHz, CDCl3) δ 9.69 (s, 1H), 9.27 (d, J=7.6 Hz, 1H), 8.93 (s, 1H), 7.89 (s, 1H), 7.79 (s, 1H), 7.70 (d, J=8.0 Hz, 1H), 7.58-7.50 (m, 3H), 6.93 (d, J=7.6 Hz, 1H), 5.36 (s, 1H), 2.59 (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-96fd9feaa9b34cb392fbfa267860565e
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08987250B2

Reaction notes

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