Ammonium Hydroxide → HCID 73054269, compound

HRID 75316Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([NH:8][C@H:9]([C:11]2[N:16]=[C:15]3[CH:17]=[CH:18][N:19]([CH3:20])[C:14]3=[CH:13][C:12]=2[C:21]2[N:25]([CH3:26])[N:24]=[CH:23][CH:22]=2)[CH3:10])[C:5]([C:27]#[N:28])=[CH:4][N:3]=1.[OH-].[NH4+:30]>O1CCOCC1>[NH2:30][C:2]1[N:7]=[C:6]([NH:8][C@H:9]([C:11]2[N:16]=[C:15]3[CH:17]=[CH:18][N:19]([CH3:20])[C:14]3=[CH:13][C:12]=2[C:21]2[N:25]([CH3:26])[N:24]=[CH:23][CH:22]=2)[CH3:10])[C:5]([C:27]#[N:28])=[CH:4][N:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of (S)-2-chloro-4-((1-(1-methyl-6-(1-methyl-1H-pyrazol-5-yl)-1H-pyrrolo[3,2-b]pyridin-5-yl)ethyl)amino)pyrimidine-5-carbonitrile (60 mg, 0.153 mmol) in dioxane (1 mL) and ammonium hydroxide (1 mL, 7.19 mmol) was heated at 100° C. in a microwave reactor for 1 hour. The reaction mixture was subsequently concentrated and purified by preparative HPLC (basic mode, 25% to 50% ACN/water gradient) to give the title compound as an off-white solid (14.2 mg, 24.9%). 1H NMR (500 MHz, CD3OD) δ ppm 1.41 (br s, 3 H), 3.59-3.74 (m, 3 H), 3.86-3.92 (m, 3 H), 5.16-5.36 (m, 1 H), 6.39-6.50 (m, 1 H), 6.63-6.73 (m, 1 H), 7.57-7.67 (m, 2 H), 7.77-7.88 (m, 1H), 8.04-8.13 (m, 1H); ESI-MS m/z [M+H]+ calc'd for C19H19N9, 374.18; found 374.3.

Workup

concentrationThe reaction mixture was subsequently concentrated
custompurified by preparative HPLC (basic mode, 25% to 50% ACN/water gradient)

Sources & evidence

ORD record: ord-da843c1a95244ff4b8e9b37340f64eaf
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08835420B2

Reaction notes

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