Sodium Hydroxide → HCID 71611843, compound

HRID 2409076Notes

Reaction equation

[CH:1]1([C:4]2[NH:8][N:7]=[C:6]([NH:9][C:10]3[CH:15]=[CH:14][N:13]=[C:12]([NH:16][C@H:17]([C:19]4[N:24]=[C:23]5[CH:25]=[CH:26][N:27](S(C6C=CC(C)=CC=6)(=O)=O)[C:22]5=[CH:21][C:20]=4[F:38])[CH3:18])[N:11]=3)[CH:5]=2)[CH2:3][CH2:2]1.[OH-].[Na+]>CO>[CH:1]1([C:4]2[NH:8][N:7]=[C:6]([NH:9][C:10]3[CH:15]=[CH:14][N:13]=[C:12]([NH:16][C@H:17]([C:19]4[N:24]=[C:23]5[CH:25]=[CH:26][NH:27][C:22]5=[CH:21][C:20]=4[F:38])[CH3:18])[N:11]=3)[CH:5]=2)[CH2:3][CH2:2]1

Participants

Conditions

Temperature: 50 °C

Procedure

To a mixture of (S)—N4-(5-cyclopropyl-1H-pyrazol-3-yl)-N2-(1-(6-fluoro-1-tosyl-1H-pyrrolo[3,2-b]pyridin-5-yl)ethyl)pyrimidine-2,4-diamine (120 mg, 0.226 mmol) in MeOH (10 mL) was added aqueous NaOH (18 mg, 2 mL H2O). The mixture was heated at 50° C. for 5 h. The reaction mixture was quenched by adding a sat'd, aq. NH4Cl solution and extracted with EtOAc (50 mL×3), dried (Na2SO4), filtered, and concentrated under reduced pressure. The residue was purified by preparative HPLC to afford (S)—N4-(5-cyclopropyl-1H-pyrazol-3-yl)-N2-(1-(6-fluoro-1H-pyrrolo[3,2-b]pyridin-5-yl)ethyl)pyrimidine-2,4-diamine as white solid (25 mg, 30%). 1H NMR (500 MHz, MeOD) δ 7.79-7.81 (d, 1H), 7.53-7.59 (m, 2H), 6.62 (s, 1H), 6.03-6.27 (m, 2H), 5.54-5.59 (m, 1H), 1.95 (m, 1H), 1.59 (m, 3H), 1.01 (m, 2H), 0.78 (m, 2H); MS (ESI): m/z=379.1 [M+1]+.

Workup

customThe reaction mixture was quenched
additionby adding a sat'd, aq. NH4Cl solution
extractionextracted with EtOAc (50 mL×3)
dry with materialdried (Na2SO4)
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe residue was purified by preparative HPLC

Sources & evidence

ORD record: ord-ff0ad3fd34be464ca3fd6c0e804f3a52
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08815877B2

Reaction notes

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