Water → HCID 57463168, compound

HRID 1783818Notes

Reaction equation

CC1(C)[O:6][C@H:5]([CH2:7][N:8]2[CH2:13][CH2:12][CH2:11][C@@H:10]([NH:14][C:15]3[N:20]=[C:19]([C:21]4[N:28]5[C:24]([S:25][CH:26]=[CH:27]5)=[N:23][C:22]=4[C:29]4[CH:34]=[CH:33][CH:32]=[C:31]([O:35][CH3:36])[CH:30]=4)[CH:18]=[CH:17][N:16]=3)[CH2:9]2)[CH2:4][O:3]1.O.FC(F)(F)C(O)=O.C(=O)([O-])[O-].[K+].[K+]>CO>[CH3:36][O:35][C:31]1[CH:30]=[C:29]([C:22]2[N:23]=[C:24]3[N:28]([C:21]=2[C:19]2[CH:18]=[CH:17][N:16]=[C:15]([NH:14][C@@H:10]4[CH2:11][CH2:12][CH2:13][N:8]([CH2:7][C@@H:5]([OH:6])[CH2:4][OH:3])[CH2:9]4)[N:20]=2)[CH:27]=[CH:26][S:25]3)[CH:34]=[CH:33][CH:32]=1

Participants

Conditions

Temperature: 50 °C

Procedure

The N-((3R)-1-{[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl}piperidin-3-yl)-4-[6-(3-methoxyphenyl)imidazo[2,1-b][1,3]thiazol-5-yl]pyrimidin-2-amine (150 mg, 0.288 mmol) was dissolved in MeOH (10 ml) and water (1.2 ml) and treated with trifluoroacetic acid (90 uL). The mixture was stirred at 50° C. overnight (18 hours). The mixture was neutralized with potassium carbonate (160 mg) and the volatiles were removed in vacuo. The product was purified by flash chromatography (6:1 EtOAc/MeOH), affording the title compound as an off-white solid (120 mg, 87%). M.p.=106-108° C. 400 MHz 1H NMR (DMSO-d6) δ: 8.72 (br. s, 1H), 8.08 (d, J=5.5 Hz, 1H), 7.44 (d, J=4.4 Hz, 1H), 7.36 (t, J=7.9 Hz, 1H), 7.16-7.10 (m, 2H), 7.06-6.97 (m, 2H), 6.36 (d, J=5.5 Hz, 1H), 4.40-4.15 (m, 1H), 4.02-3.90 (m, 1H), 3.77 (s, 3H), 3.68-3.56 (m, 2H), 3.40-3.28 (m, 2H), 3.05-2.95 (m, 1H), 2.80-2.64 (m, 1H), 2.42 (br. s, 1H), 2.32 (br. s, 1H), 2.14 (br. s, 1H), 1.90-1.80 (m, 1H), 1.75-1.65 (m, 1H), 1.60-1.45 (m, 1H), 1.45-1.30 (m, 1H). LCMS: 481 [M+H].

Workup

customthe volatiles were removed in vacuo
customThe product was purified by flash chromatography (6:1 EtOAc/MeOH)

Sources & evidence

ORD record: ord-39add21eac73415d98cd6896ebf24499
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07501430B2

Reaction notes

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