Triethylamine → HCID 10178067, compound

HRID 1827171Notes

Reaction equation

HRID 1827171 reaction equation
[CH:1]1([C:4]2[CH:21]=[CH:20][C:7]([CH2:8][O:9][C:10]([N:12]3[CH2:17][CH2:16][CH:15]([CH2:18][NH2:19])[CH2:14][CH2:13]3)=[O:11])=[CH:6][CH:5]=2)[CH2:3][CH2:2]1.Cl[C:23]1[N:28]=[CH:27][C:26]([F:29])=[CH:25][N:24]=1.C(N(CC)CC)C>CN(C=O)C>[CH:1]1([C:4]2[CH:21]=[CH:20][C:7]([CH2:8][O:9][C:10]([N:12]3[CH2:17][CH2:16][CH:15]([CH2:18][NH:19][C:23]4[N:28]=[CH:27][C:26]([F:29])=[CH:25][N:24]=4)[CH2:14][CH2:13]3)=[O:11])=[CH:6][CH:5]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 5834662-Chloro-5-fluoropyrimidineHCID 22135747HCID 22135747, compound

Product 1

HCID 10178067HCID 10178067, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of (4-cyclopropyl-benzyl)-4-(aminomethyl)piperidine-1-carboxylate (0.10 g, 0.35 mmol), 2-chloro-5-fluoro-pyrimidine (EXAMPLE 71, Step 1, 0.046 g, 0.35 mmol) and triethylamine (0.097 mL, 0.69 mmol) in DMF (1 mL) was heated at 100° C. for 6 h, then concentrated in vacuo. The residue was purified by silica gel chromatography (CH2Cl2/IPA/hexanes) to give 4-[(5-fluoro-pyrimidin-2-ylamino)-methyl]-piperidine-1-carboxylic acid-4-cyclopropyl-benzyl ester. M.S.(M+1):385.31

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by silica gel chromatography (CH2Cl2/IPA/hexanes)

Sources & evidence

ORD record
ord-b6c040812f4e41839b4e1f78abac1248
Source dataset
uspto-grants-2006_05
Patent number
US07053089B2

Reaction notes

Loading…