Triethylamine → HCID 71765594, compound

HRID 626849Notes

Reaction equation

Cl.Cl.Cl.[NH2:4][C:5]1[N:10]=[CH:9][N:8]=[C:7]2[N:11]([CH:15]([C:17]3[CH:18]=[C:19]([Cl:35])[C:20]([C:33]#[N:34])=[C:21]4[C:27]=3[O:26][CH:25]([CH3:28])[CH2:24][N:23]([CH:29]3[CH2:32][NH:31][CH2:30]3)[CH2:22]4)[CH3:16])[N:12]=[C:13]([CH3:14])[C:6]=12.C(N(CC)CC)C.[CH3:43][C:44]1([CH3:47])[CH2:46][O:45]1>CN(C)C=O>[NH2:4][C:5]1[N:10]=[CH:9][N:8]=[C:7]2[N:11]([CH:15]([C:17]3[CH:18]=[C:19]([Cl:35])[C:20]([C:33]#[N:34])=[C:21]4[C:27]=3[O:26][CH:25]([CH3:28])[CH2:24][N:23]([CH:29]3[CH2:32][N:31]([CH2:43][C:44]([OH:45])([CH3:47])[CH3:46])[CH2:30]3)[CH2:22]4)[CH3:16])[N:12]=[C:13]([CH3:14])[C:6]=12

Participants

Conditions

Temperature: 85 °C

Procedure

9-[1-(4-Amino-3-methyl-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-4-azetidin-3-yl-7-chloro-2-methyl-2,3,4,5-tetrahydro-1,4-benzoxazepine-6-carbonitrile trishydrochloride (0.015 g, 0.034 mmol) was dissolved in N,N-dimethylformamide (1.0 mL) and triethylamine (0.025 mL, 0.18 mmol), and 2,2-dimethyloxirane (0.050 g) was added. The reaction was heated to 85° C. stirred for 4 h. The reaction was concentrated in vacuo, and the product was purified without workup by prep HPLC on a C-18 column eluting water:acetonitrile gradient buffered pH 10 to give the title compound as two diastereomers: Peak #1 (Example 54) (0.002 g, 13%): LCMS calculated for C26H34ClN8O2 (M+H)+: m/z=525.2; found: 525.2; Peak #2 (Example 55) (0.002 g 13%): LCMS calculated for C26H34ClN8O2 (M+H)+: m/z=525.2; found: 525.2.

Workup

concentrationThe reaction was concentrated in vacuo
customthe product was purified without workup by prep HPLC on a C-18 column
washeluting water

Sources & evidence

ORD record: ord-b2562c2121cb4768955935db97dca329
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09309251B2

Reaction notes

Loading…