Sodium Hydroxide → HCID 178461999, compound

HRID 75317Notes

Reaction equation

[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([NH:10][C@H:11]([C:13]2[N:18]=[C:17]3[CH:19]=[CH:20][N:21]([CH3:22])[C:16]3=[CH:15][C:14]=2[N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)[CH3:12])[N:5]=[C:4](S(C)(=O)=O)[N:3]=1.[OH-:33].[Na+]>C1COCC1>[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([NH:10][C@H:11]([C:13]2[N:18]=[C:17]3[CH:19]=[CH:20][N:21]([CH3:22])[C:16]3=[CH:15][C:14]=2[N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)[CH3:12])[N:5]=[C:4]([OH:33])[N:3]=1

Participants

Conditions

Temperature: 50 °C

Procedure

(S)-4-Amino-6-((1-(1-methyl-6-morpholino-1H-pyrrolo[3,2-b]pyridin-5-yl)ethyl)amino)-2-(methylsulfonyl)pyrimidine-5-carbonitrile (66 mg, 0.145 mmol) in THF (2 mL) was combined with sodium hydroxide (0.289 mL, 0.289 mmol) to give a yellow solution, which was heated to 50° C. and stirred for 3 hours. The product was purified by LC/MS using a 5-30% CH3CN gradient in H2O with 0.035% formic acid. The pure fractions were combined and lyophilized to give a formic acid salt of the title compound as a white solid (7 mg, 12%). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.32-1.46 (m, 3 H), 2.70-2.85 (m, 2H), 3.00-3.13 (m, 2 H), 3.81 (s, 8 H), 5.67-5.86 (m, 1 H), 6.43-6.53 (m, 1 H), 7.05-7.23 (m, 1 H), 7.27-7.45 (m, 2 H), 7.52-7.64 (m, 1 H), 7.85-7.94 (m, 1 H); ESI-MS m/z [M+H]+ calc'd for C19H22N8O2, 395.4; found 395.5.

Workup

customto give a yellow solution, which
customThe product was purified by LC/MS

Sources & evidence

ORD record: ord-96108866c2104fb482a4c38667e5019d
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08835420B2

Reaction notes

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