Water → HCID 178437526, compound

HRID 718641Notes

Reaction equation

Cl[C:2]1[N:7]=[CH:6][C:5]([C:8]2[N:12]3[N:13]=[CH:14][CH:15]=[C:16]([N:17]4[CH2:22][CH2:21][O:20][CH2:19][CH2:18]4)[C:11]3=[N:10][C:9]=2/[CH:23]=[CH:24]/[C:25]2[CH:34]=[CH:33][C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[N:26]=2)=[CH:4][CH:3]=1.[N:35]1[N:36]=[C:37]([SH:40])[NH:38][CH:39]=1.CC(C)([O-])C.[K+].O>CC(N(C)C)=O>[N:35]1[N:36]=[C:37]([S:40][C:2]2[N:7]=[CH:6][C:5]([C:8]3[N:12]4[N:13]=[CH:14][CH:15]=[C:16]([N:17]5[CH2:22][CH2:21][O:20][CH2:19][CH2:18]5)[C:11]4=[N:10][C:9]=3/[CH:23]=[CH:24]/[C:25]3[CH:34]=[CH:33][C:32]4[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=4)[N:26]=3)=[CH:4][CH:3]=2)[NH:38][CH:39]=1

Participants

Conditions

Temperature: 140 °C

Procedure

A solution of compound 49a (0.50 g, 1.1 mmol) in DMA (3 mL) was treated with 4H-1,2,4-triazole-3-thiol (0.16 g, 1.6 mmol) and potassium tert-butoxide (0.24 g, 2.1 mmol). The resulting mixture was stirred at 140° C. for 3 h, allowed to cool to rt and treated with water (10 mL). The solids obtained were collected by filtration and purified by RP Prep-HPLC. The title compound 22 was obtained as a yellow solid. 1H-NMR (300 MHz, DMSO-d6) δ (ppm): 14.65 (s, 1H), 8.86 (s, 1H), 8.74 (s, 1H), 8.31 (d, J=8.7 Hz, 1H), 8.13 (d, J=5.7 Hz, 1H), 8.08-8.05 (m, 1H), 7.99-7.92 (m, 3H), 7.81-7.70 (m, 3H), 7.58-7.52 (m, 1H), 7.36 (d, J=7.8 Hz, 1H), 6.44 (d, J=6.0 Hz, 1H), 4.15-4.05 (m, 4H), 3.85-3.75 (m, 4H). Mass Spectrum (LCMS, ESI pos.): Calcd. for C28H23N9OS: 534.2 (M+H). Found: 534.2.

Workup

temperatureto cool to rt
customThe solids obtained
filtrationwere collected by filtration
custompurified by RP Prep-HPLC

Sources & evidence

ORD record: ord-bc3839e1d7e947b98bcb015128269c11
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09193736B2

Reaction notes

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