Sodium Hydroxide → HCID 86700189, compound

HRID 879379Notes

Reaction equation

[C:1]([O:5][C@@H:6]([C:12]1[C:45]([CH3:46])=[CH:44][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]C(C4CCCCC4)=O)[CH:29]=[CH:28]5)[CH:20]=3)[S:18][C:14]=2[C:13]=1[C:47]1[CH:52]=[CH:51][C:50]([Cl:53])=[CH:49][CH:48]=1)[C:7]([O:9]CC)=[O:8])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>C1COCC1.CO>[NH2:35][C:30]1[CH:29]=[CH:28][C:27]2[C:32](=[CH:33][CH:34]=[C:25]([C:21]3[CH:20]=[C:19]([C:17]4[S:18][C:14]5[C:13]([C:47]6[CH:48]=[CH:49][C:50]([Cl:53])=[CH:51][CH:52]=6)=[C:12]([C@H:6]([O:5][C:1]([CH3:3])([CH3:2])[CH3:4])[C:7]([OH:9])=[O:8])[C:45]([CH3:46])=[CH:44][C:15]=5[N:16]=4)[CH:24]=[CH:23][N:22]=3)[CH:26]=2)[N:31]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a stirred solution of (S)-ethyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-2-(2-(2-(cyclohexanecarboxamido)quinolin-6-yl)pyridin-4-yl)-5-methylbenzo[d]thiazol-6-yl)acetate (12.0 mg, 0.016 mmol) in THF (0.4 mL) and methanol (0.4 mL) was added 1N NaOH solution (0.4 mL, excess). The reaction mixture was stirred at 50° C. for 2 h 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 C34H30ClN4O3S: 609.2; found: 609.2. 1H NMR (400 MHz, CDCl3) δ 8.90 (d, J=5.6 Hz, 1H), 8.51 (s, 1H), 8.45 (s, 1H), 8.29 (d, J=8.4 Hz, 1H), 8.16 (d, J=9.2 Hz, 1H), 8.06 (d, J=0.8 Hz, 1H), 8.00 (s, 1H), 7.90 (d, J=8.8 Hz, 1H), 7.73 (d, J=8.0 Hz, 1H), 7.59-7.45 (m, 3H), 6.94 (d, J=8.8 Hz, 1H), 5.36 (s, 1H), 2.62 (s, 3H), 1.03 (s, 9H).

Workup

custompurified by reverse phase HPLC
washeluting by 0-100% acetonitrile in H2O with 0.1% TFA

Sources & evidence

ORD record: ord-5e5bd2e7e48449d7a5b1ad33d6173867
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08987250B2

Reaction notes

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