Hydrochloric Acid → HCID 57936250, compound

HRID 1435002Notes

Reaction equation

HRID 1435002 reaction equation
[CH3:1][C:2]1([CH3:28])[CH2:7][CH:6]([NH:8][C:9]2[N:14]=[C:13]([C:15]3[CH:20]=[CH:19][C:18]([CH2:21][CH2:22]C(O)=O)=[CH:17][CH:16]=3)[CH:12]=[CH:11][N:10]=2)[CH2:5][C:4]([CH3:27])([CH3:26])[NH:3]1.C([N:31](CC)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.Cl>C(#N)C.O>[NH2:31][CH2:22][CH2:21][C:18]1[CH:17]=[CH:16][C:15]([C:13]2[CH:12]=[CH:11][N:10]=[C:9]([NH:8][CH:6]3[CH2:7][C:2]([CH3:1])([CH3:28])[NH:3][C:4]([CH3:26])([CH3:27])[CH2:5]3)[N:14]=2)=[CH:20][CH:19]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 579362343-{4-[2-(2,2,6,6-Tetramethyl-piperidin-4-ylamino)-pyrimidin-4-yl]-phenyl}-propionic acid

Product 1

HCID 57936250HCID 57936250, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

A suspension of 3-{4-[2-(2,2,6,6-tetramethyl-piperidin-4-ylamino)-pyrimidin-4-yl]-phenyl}-propionic acid (100 mg, 0.26 mmol) (Step A of Example 185), triethylamine (37 μl, 0.26 mmol) and diphenylphosphoryl azide (57 μl, 0.26 mmol) in 3 ml acetonitrile was heated for 18 hours at 70° C. Then, 1.2 ml 0.4N-HCl was added and the mixture was stirred for 1 hour at ambient temperature. The solution was diluted with water, extracted with ether and the aqueous phase was made basic with 2N-NaOH. Extraction with EtOAc and purification with preparative HPLC gave the title compound. Yield: 24 mg (26%).

Workup

  1. extractionextracted with ether
  2. extractionExtraction
  3. customwith EtOAc and purification with preparative HPLC

Sources & evidence

ORD record
ord-261fbee9f3584aabb7e09d440ff28f08
Source dataset
uspto-grants-2009_11
Patent number
US07615562B2

Reaction notes

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