Triethylamine → HCID 45141621, compound

HRID 1470299Notes

Reaction equation

HRID 1470299 reaction equation
Cl.Cl.[NH2:3][C:4]1([CH2:10][NH:11][C:12](=[O:20])[C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)[CH2:9][CH2:8][NH:7][CH2:6][CH2:5]1.Cl[C:22]1[C:23]2[CH:30]=[CH:29][NH:28][C:24]=2[N:25]=[CH:26][N:27]=1.C(N(CC)CC)C>C(O)CCC>[NH2:3][C:4]1([CH2:10][NH:11][C:12](=[O:20])[C:13]2[CH:14]=[CH:15][C:16]([Cl:19])=[CH:17][CH:18]=2)[CH2:9][CH2:8][N:7]([C:22]2[C:23]3[CH:30]=[CH:29][NH:28][C:24]=3[N:25]=[CH:26][N:27]=2)[CH2:6][CH2:5]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 53566827H-Pyrrolo(2,3-d)pyrimidine, 4-chloro-HCID 45139442HCID 45139442, compound

Product 1

HCID 45141621HCID 45141621, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
100 °C

Procedure

A degassed mixture of crude N-(4-amino-piperidin-4-ylmethyl)-4-chloro-benzamide dihydrochloride (6.1 mg), 4-chloro-7H-pyrrolo[2,3-d]pyrimidine (2.6 mg, 0.016 mmol), triethylamine (16 μL, 0.09 mmol) and n-butanol (0.3 mL) was stirred at 100° C. for 17 hours. The solvents were concentrated. The crude mixture was first purified on an SCX-II acidic resin, eluting with methanol then 2M ammonia-methanol, and then by preparative TLC, eluting with 15% methanol-dichloromethane, to give N-[4-amino-1-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-piperidin-4-ylmethyl]-4-chloro-benzamide (3.3 mg, 0.009 mmol, 69% over 2 steps). LC-MS (LCT2) m/z 385 [M+H+], Rt 2.58 min.

Workup

  1. concentrationThe solvents were concentrated
  2. customThe crude mixture was first purified on an SCX-II acidic resin
  3. washeluting with methanol
  4. wash2M ammonia-methanol, and then by preparative TLC, eluting with 15% methanol-dichloromethane

Sources & evidence

ORD record
ord-648e8e10d6114820aac7b06dea0d5f3c
Source dataset
uspto-grants-2015_04
Patent number
US09006430B2

Reaction notes

Loading…