Phosphoric Acid → 3-[4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]heptanenitrile phosphate

HRID 1910994Notes

Reaction equation

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

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 3-[4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]heptanenitrile (0.363 g, 1.23 mmol) in isopropyl alcohol (8.0 mL) was added phosphoric acid (0.133 g, 1.36 mmol) in 1.0 mL isopropyl alcohol at 60° C. The mixture was heated at 60° C. for 1 hour, then cooled to room temperature. The precipitate was filtered off and air dried, rinsed with ethyl ether, and then air dried further to provide the desired phosphoric acid salt (418 mg, 86.5%). 1H NMR (DMSO-d6, 400 MHz) δ 12.10 (1H, s), 8.78 (1H, s), 8.66 (1H, s), 8.36 (1H, s), 7.58 (1H, m), 6.97 (1H, m), 4.71 (1H, m), 3.18 (1H, m), 3.17 (1H, m), 1.93 (1H, m), 1.82 (1H, m), 1.21 (3H, m), 0.95 (1H, m), 0.78 (3H, t, J=7.2 Hz) ppm.

Workup

temperaturecooled to room temperature
filtrationThe precipitate was filtered off
customair dried
washrinsed with ethyl ether
customair dried further

Sources & evidence

ORD record: ord-cf27465a8fec4853b0b591dee6ae9679
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08604043B2

Reaction notes

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