Water → HCID 58014541, compound

HRID 1876864Notes

Reaction equation

HRID 1876864 reaction equation
[C:1]([CH2:3][CH:4]([N:10]1[CH:14]=[C:13]([C:15]2[CH:20]=[CH:19][N:18]=[C:17]([NH:21][C:22]3[CH:23]=[C:24]([CH:28]=[CH:29][CH:30]=3)C(O)=O)[N:16]=2)[CH:12]=[N:11]1)[CH:5]1[CH2:9][CH2:8][CH2:7][CH2:6]1)#[N:2].C1C=CC(OP(OC2C=CC=CC=2)([N:40]=[N+]=[N-])=O)=CC=1.C(N(CC)CC)C.O>O1CCOCC1>[NH2:40][C:24]1[CH:23]=[C:22]([NH:21][C:17]2[N:16]=[C:15]([C:13]3[CH:12]=[N:11][N:10]([CH:4]([CH:5]4[CH2:9][CH2:8][CH2:7][CH2:6]4)[CH2:3][C:1]#[N:2])[CH:14]=3)[CH:20]=[CH:19][N:18]=2)[CH:30]=[CH:29][CH:28]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 123414Diphenylphosphoryl azideHCID 58014442HCID 58014442, compound

Product 1

HCID 58014541HCID 58014541, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 3-(4-(1-(2-cyano-1-cyclopentylethyl)-1H-pyrazol-4-yl)pyrimidin-2-ylamino)benzoic acid (228 mg, 0.566 mmol), and diphenylphosphonic azide (0.18 mL, 0.85 mmol), triethylamine (0.16 mL, 1.1 mmol) in 1,4-dioxane (4.2 mL) was stirred at room temperature overnight. To the resulting mixture was added water (0.36 mL). The reaction was refluxed overnight. The crude racemic mixture was used directly in next step. An analytically pure sample was obtained by RP-HPLC (pH 2). LCMS (M+H) 374.1.

Workup

  1. temperatureThe reaction was refluxed overnight
  2. customAn analytically pure sample was obtained by RP-HPLC (pH 2)

Sources & evidence

ORD record
ord-54f0e039c337411eaf7abe8b79f69c47
Source dataset
uspto-grants-2012_11
Patent number
US08309718B2

Reaction notes

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