Trichloroacetyl chloride → HCID 178511092, compound

HRID 449777Notes

Reaction equation

HRID 449777 reaction equation
[CH:1]1([CH:6]([N:11]2[CH:15]=[C:14]([C:16]3[C:17]4[C:25](=[O:26])[CH2:24][NH:23][C:18]=4[N:19]=[C:20]([OH:22])[N:21]=3)[CH:13]=[N:12]2)[CH2:7][C:8]([NH2:10])=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.ClC(Cl)(Cl)C(Cl)=O.CC#N.O>C(Cl)Cl>[CH:1]1([C@H:6]([N:11]2[CH:15]=[C:14]([C:16]3[C:17]4[C:25](=[O:26])[CH2:24][NH:23][C:18]=4[N:19]=[C:20]([OH:22])[N:21]=3)[CH:13]=[N:12]2)[CH2:7][C:8]#[N:10])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 6420Trichloroacetyl chlorideHCID 8471TriethylamineHCID 18373917Acetonitrile--water (1/1)HCID 178513882HCID 178513882, compound

Product 1

HCID 178511092HCID 178511092, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-cyclopentyl-3-[4-(2-hydroxy-5-oxo-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]propanamide (0.006 g, 0.02 mmol) in methylene chloride (0.5 mL) containing triethylamine (20 TL, 0.2 mmol) was added trichloroacetyl chloride (20 TL, 0.2 mmol). When the reaction was complete, preparative HPLC-MS (MeCN/H2O containing 0.15% NH4OH) was used to afford purified product (3 mg, 52%). 1H NMR (400 MHz, d6-DMSO): δ 11.39 (br s, 1H), 9.37 (s, 1H), 8.77 (s, 1H), 8.63 (s, 1H), 4.68-4.59 (m, 1H), 3.94 (s, 2H), 3.19-3.15 (m, 2H), 2.42-2.30 (m, 1H), 1.86-1.75 (m, 1H), 1.69-1.20 (m, 6H), 1.18-1.05 (m, 1H); LCMS (M+H)+: 339.1.

Workup

  1. customto afford
  2. custompurified product (3 mg, 52%)

Sources & evidence

ORD record
ord-6fc1c005147e441ebccdc4057355899a
Source dataset
uspto-grants-2013_07
Patent number
US08486902B2

Reaction notes

Loading…