Acetone → HCID 86677816, compound

HRID 1499892Notes

Reaction equation

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

Participants

Reactant 2

HCID 180Acetone

HCID 86677817HCID 86677817, compound

Product 1

HCID 86677816HCID 86677816, compoundYield 65%

Procedure

The desired compound was prepared according to the procedure of Example 213 using 4-[1-(4-amino-5-methyl-7H-pyrrolo[2,3-d]pyrimidin-7-yl)ethyl]-2-azetidin-3-yl-6-chloro-3-ethoxybenzonitrile instead of 4-[1-(4-amino-3-methyl-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-2-azetidin-3-yl-6-chloro-3-ethoxybenzonitrile and acetone instead of formaldehyde as the starting materials in 65% yield. The product was isolated as a single enantiomer. 1H NMR (300 MHz, dmso) δ 7.95 (s, 1H), 7.19 (s, 1H), 7.16-7.13 (m, 1H), 6.58 (s, 2H), 6.11 (q, J=7.1 Hz, 1H), 4.04-3.67 (m, 5H), 3.04-2.92 (m, 2H), 2.36 (s, 3H), 2.27-2.12 (m, 1H), 1.69 (d, J=7.1 Hz, 3H), 1.30 (t, J=6.9 Hz, 3H), 0.85 (dd, J=6.1, 1.8 Hz, 6H). LCMS for C24H30ClN6O (M+H)+: m/z=453.2; Found: 453.3.

Workup

customThe product was isolated as a single enantiomer

Sources & evidence

ORD record: ord-deb19ae49b814479bb3926b99ffd4a87
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09199982B2

Reaction notes

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