Diisopropylethylamine → HCID 90109389, compound

HRID 521729Notes

Reaction equation

[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[C@:7]12[CH2:15][NH:14][CH2:13][C@H:12]1[CH2:11][S:10][C:9]([NH:16][C:17](=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[N:8]2.Cl[C:26]1[N:31]=[C:30]([C:32]([OH:35])([CH3:34])[CH3:33])[C:29]([F:36])=[CH:28][N:27]=1.C(N(C(C)C)CC)(C)C>O1CCOCC1>[F:36][C:29]1[C:30]([C:32]([OH:35])([CH3:33])[CH3:34])=[N:31][C:26]([N:14]2[CH2:13][C@@H:12]3[C@@:7]([C:2]4[CH:3]=[N:4][CH:5]=[CH:6][N:1]=4)([N:8]=[C:9]([NH:16][C:17](=[O:24])[C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[S:10][CH2:11]3)[CH2:15]2)=[N:27][CH:28]=1

Participants

Conditions

Temperature: 110 °C

Procedure

N-[(4aR,7aR)-7a-pyrazin-2-yl-4a,5,6,7-tetrahydro-4H-pyrrolo[3,4-d][1,3]thiazin-2-yl]benzamide (231 mg, 0.680 mmol) is dissolved in 1,4-dioxane (4 mL). 2-(2-Chloro-5-fluoro-pyrimidin-4-yl)propan-2-ol (648.60 mg, 3.40 mmol) and diisopropylethylamine (653 μL, 3.74 mmol) are added. The reaction is heated at 110° C. for 6 hours then cooled to room temperature and concentrated under reduced pressure. The resulting residue is purified by silica gel column chromatography using a 0-5% gradient of 0.14 M ammonia/methanol solution in dichloromethane to give the title compound (330 mg, 98%). ES/MS (m/e): 494 (M+1).

Workup

temperaturethen cooled to room temperature
concentrationconcentrated under reduced pressure
customThe resulting residue is purified by silica gel column chromatography

Sources & evidence

ORD record: ord-fd78984dc90f466aa08f55c6b5886902
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09328124B2

Reaction notes

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