Phosphoric Acid → 4-[1-(1-methyl-2-{4-[(1-methyl-1H-pyrazol-3-yl)sulfonyl]piperazin-1-yl}ethyl)-1H-pyrazol-4-yl]-7H-pyrrolo[2,3-d]pyrirnidine phosphoric acid salt

HRID 1772782Notes

Reaction equation

HRID 1772782 reaction equation
[CH3:1][CH:2]([N:19]1[CH:23]=[C:22]([C:24]2[C:25]3[CH:32]=[CH:31][NH:30][C:26]=3[N:27]=[CH:28][N:29]=2)[CH:21]=[N:20]1)[CH2:3][N:4]1[CH2:9][CH2:8][N:7]([S:10]([C:13]2[CH:17]=[CH:16][N:15]([CH3:18])[N:14]=2)(=[O:12])=[O:11])[CH2:6][CH2:5]1.[P:33](=[O:37])([OH:36])([OH:35])[OH:34]>C(O)(C)C>[P:33](=[O:34])([OH:37])([OH:36])[OH:35].[CH3:1][CH:2]([N:19]1[CH:23]=[C:22]([C:24]2[C:25]3[CH:32]=[CH:31][NH:30][C:26]=3[N:27]=[CH:28][N:29]=2)[CH:21]=[N:20]1)[CH2:3][N:4]1[CH2:5][CH2:6][N:7]([S:10]([C:13]2[CH:17]=[CH:16][N:15]([CH3:18])[N:14]=2)(=[O:12])=[O:11])[CH2:8][CH2:9]1

Participants

4

Reactant 2

HCID 1004Phosphoric AcidHCID 581809464-[1-(1-methyl-2-{4-[(1-methyl-1H-pyrazol-3-yl)sulfonyl]piperazin-1-yl}ethyl)-1H-pyrazol-4-yl]-7H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 670548834-[1-(1-methyl-2-{4-[(1-methyl-1H-pyrazol-3-yl)sulfonyl]piperazin-1-yl}ethyl)-1H-pyrazol-4-yl]-7H-pyrrolo[2,3-d]pyrirnidine phosphoric acid saltYield 74.9%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent2×

Conditions

Temperature
60 °C

Procedure

A suspension of 4-[1-(1-methyl-2-{4-[(1-methyl-1H-pyrazol-3-yl)sulfonyl]piperazin-1-yl}ethyl)-1H-pyrazol-4-yl]-7H-pyrrolo[2,3-d]pyrimidine (0.165 g, 0.362 mmol) in isopropyl alcohol (60 mL) was heated at 60° C. until becoming clear. Phosphoric acid (0.0373 g, 0.373 mmol) in isopropyl alcohol (1.0 mL) was added to the solution at 60° C. The solution was cooled down but no precipitation formed. Solvents were reduced in vacuo until white solid precipitated and held at RT for 30 min. The solid was filtered off, air dried, rinsed with some Et2O and again air dried to give a phosphoric acid salt (150 mg, 74.8%). The number of phosphoric acids in the salt was not determined. LCMS calculated for C20H26N9O2S(M+H)+: m/z=456.2 (free base); Found: 456.4. 1H NMR (400 MHz, DMSO-d6): δ 8.62 (1H, s), 8.59 (1H, s), 8.22 (1H, s), 7.86 (1H, d, J=2.2 Hz), 7.54 (1H, d, J=3.6 Hz), 6.91 (1H, d, J=3.6 Hz), 6.58 (1H, d, J=2.2 Hz), 4.63 (1H, m), 3.82 (3H, s), 2.85˜2.78 (5H, m), 2.61˜2.54 (3H, m), 2.36 (2H, m), 1.40 (3H, d, J=6.4 Hz) ppm.

Workup

  1. temperatureThe solution was cooled down
  2. customno precipitation
  3. customformed
  4. customprecipitated
  5. filtrationThe solid was filtered off
  6. customair dried
  7. washrinsed with some Et2O and again air
  8. customdried

Sources & evidence

ORD record
ord-efe62f40f2204eaeb53f5e2c0f929fed
Source dataset
uspto-grants-2016_02
Patent number
US09249145B2

Reaction notes

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