1-Hydroxybenzotriazole → HCID 70817680, compound

HRID 82129Notes

Reaction equation

HRID 82129 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH2:12][OH:13])[C:9]([OH:11])=O)=[CH:4][CH:3]=1.[NH2:14][C:15]1[CH:16]=[C:17]([C:21]([C:23]2[C:31]3[CH:30]=[N:29][CH:28]=[N:27][C:26]=3[N:25]([CH:32]([CH3:34])[CH3:33])[CH:24]=2)=[O:22])[CH:18]=[N:19][CH:20]=1.C(N(C(C)C)CC)(C)C.CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([CH2:12][OH:13])[C:9]([NH:14][C:15]2[CH:20]=[N:19][CH:18]=[C:17]([C:21]([C:23]3[C:31]4[CH:30]=[N:29][CH:28]=[N:27][C:26]=4[N:25]([CH:32]([CH3:34])[CH3:33])[CH:24]=3)=[O:22])[CH:16]=2)=[O:11])=[CH:6][CH:7]=1

Participants

7

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 126063102-(4-Chlorophenyl)-3-hydroxypropanoic acidHCID 70817456(5-aminopyridin-3-yl)(7-isopropyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)methanone

Product 1

HCID 70817680HCID 70817680, compoundYield 3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

2-(4-Chloro-phenyl)-3-hydroxy-propionic acid (570 mg, 2.84 mmol) (Preparation 244) was added to a solution of (5-Amino-pyridin-3-yl)-(7-isopropyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-methanone (200 mg, 0.71 mmol) (Preparation 95) in THF (5 mL). Di-isopropyl ethylamine (0.64 mL, 3.56 mmol), EDCI.HCl (273 mg, 1.42 mmol) and HOBT (193 mg, 1.42 mmol) were added and the mixture was stirred at 25° C. for 48 hours. The reaction mixture was quenched with saturated aqueous sodium bicarbonate solution (2 mL) and extracted with ethyl acetate (3×15 mL). The combined organic layer was washed with water (5 mL), brine (5 mL), dried over sodium sulphate and evaporated in vacuo. The crude material was purified by preparative TLC (dichloromethane:methanol 93:7) to afford the title compound as a yellow solid in 3% yield, 10 mg.

Workup

  1. customThe reaction mixture was quenched with saturated aqueous sodium bicarbonate solution (2 mL)
  2. extractionextracted with ethyl acetate (3×15 mL)
  3. washThe combined organic layer was washed with water (5 mL), brine (5 mL)
  4. dry with materialdried over sodium sulphate
  5. customevaporated in vacuo
  6. customThe crude material was purified by preparative TLC (dichloromethane:methanol 93:7)

Sources & evidence

ORD record
ord-4d2638fba169438e86166e1822b0dc0d
Source dataset
uspto-grants-2014_09
Patent number
US08846698B2

Reaction notes

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