Phosphoric Acid → HCID 49779328, compound

HRID 1505478Notes

Reaction equation

HRID 1505478 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][CH2:22][CH3:23])[CH2:16][C:17]#[N:18])[CH:14]=2)=[N:3][CH:2]=1.[P:24](=[O:28])([OH:27])([OH:26])[OH:25]>C(O)(C)C>[P:24](=[O:25])([OH:28])([OH:27])[OH:26].[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][CH2:22][CH3:23])[CH2:16][C:17]#[N:18])[CH:14]=2)=[N:3][CH:2]=1

Participants

4

Reactant 2

HCID 1004Phosphoric AcidHCID 49779329HCID 49779329, compound

Product 1

HCID 49779328HCID 49779328, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent2×

Procedure

To a solution of 3-[4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]octanenitrile (from step 3, 4.50 g, 0.0146 mol) in isopropyl alcohol (80 mL, 1 mol) was added a mixture of phosphoric acid (1.43 g, 0.0146 mol) in isopropanol (5.0 mL) while solution was kept at 60° C. The phosphoric acid salt precipitated. The heating was continued but did not affect dissolution. After being cooled to room temperature, the phosphoric acid salts were filtered off, air dried, then rinsed with some diethyl ether, and air dried. MS calculated for the base, C17H21N6(M+H)+: m/z=309.183. Found: 309.3. 1H NMR (400 MHz, DMSO-d6) δ 12.10 (1H, s), 8.79 (1H, s), 8.66 (1H, s), 8.36 (1H, s), 7.58 (1H, d, J=3.6 Hz), 6.97 (1H, d, J=3.6 Hz), 4.71 (1H, m), 3.17 (2H, m), 1.94 (1H, m), 1.81 (1H, m), 1.18 (5H, m), 0.97 (1H, m), 0.78 (3H, t, J=6.8 Hz). The product was confirmed to be 99.9% pure by three different runs on reverse phase HPLC column, and having 99.7% enantiomeric excess by six different runs on chiral HPLC column.

Workup

  1. customwas kept at 60° C
  2. customThe phosphoric acid salt precipitated
  3. dissolutiondissolution
  4. filtrationthe phosphoric acid salts were filtered off
  5. customair dried
  6. washrinsed with some diethyl ether, and air
  7. customdried

Sources & evidence

ORD record
ord-4ab1be66c3164983be9501b7059f4b7d
Source dataset
uspto-grants-2015_12
Patent number
US09216984B2

Reaction notes

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