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

HRID 1505481
Notes
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Reaction equation

HRID 1505481 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 1004Phosphoric AcidHCID 498192963-[4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]heptanenitrile

Product 1

HCID 498192973-[4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]heptanenitrile phosphateYield 86.6%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent2×

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

  1. temperaturecooled to room temperature
  2. filtrationThe precipitate was filtered off
  3. customair dried
  4. washrinsed with ethyl ether
  5. customair dried further

Sources & evidence

ORD record
ord-9e8c122c0d34488cb6a9499c43e529e1
Source dataset
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09216984B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes