Potassium Carbonate → Ammonium Hydroxide

HRID 1713123Notes

Reaction equation

HRID 1713123 reaction equation
Cl.[Cl:2][C:3]1[CH:12]=[CH:11][C:10]2[CH2:9][NH:8][CH2:7][CH2:6][C:5]=2[N:4]=1.Cl[CH2:14][C:15]([N:17]1[CH2:22][CH2:21][N:20]([CH:23]2[CH2:26][CH2:25][CH2:24]2)[CH2:19][CH2:18]1)=[O:16].C([O-])([O-])=O.[K+].[K+]>CC#N>[NH4+:4].[OH-:16].[Cl:2][C:3]1[CH:12]=[CH:11][C:10]2[CH2:9][N:8]([CH2:14][C:15]([N:17]3[CH2:22][CH2:21][N:20]([CH:23]4[CH2:26][CH2:25][CH2:24]4)[CH2:19][CH2:18]3)=[O:16])[CH2:7][CH2:6][C:5]=2[N:4]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 184491652-Chloro-5,6,7,8-tetrahydro-1,6-naphthyridine hydrochlorideHCID 574205621-(Chloroacetyl)-4-cyclobutylpiperazine

Product 2

HCID 14923Ammonium HydroxideHCID 574205742-Chloro-6-[2-(4-cyclobutylpiperazin-1-yl)-2-oxoethyl]-5,6,7,8-tetrahydro-1,6-naphthyridine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 2-chloro-5,6,7,8-tetrahydro-1,6-naphthyridine hydrochloride (80 mg, 0.38 mmol), 1-(chloroacetyl)-4-cyclobutylpiperazine (82 mg, 0.38 mmol), K2CO3 (262 mg, 1.9 mmol) and KI (7 mg, 0.04 mmol) in CH3CN (15 mL) is stirred at rt overnight. The solvent is removed in vacuo and the residue is partitioned between water (10 mL) and EtOAc (20 mL). The layers are separated and the aqueous layer is extracted with EtOAc (2×10 mL). The combined extracts are dried and evaporated. The resulting oil is purified by PTLC with 100:5:0.5 DCM:MeOH:NH4OH to give the title compound as a white solid; MS (M+1): 349.2; 1H NMR (δ, CDCl3): 7.27 (d, 1H), 7.09 (d, 1H), 3.59-3.67 (m, 6H), 3.38 (s, 2H), 3.01 (t, 2H), 2.87 (t, 2H), 2.64-2.73 (m, 1H), 2.28 (q, 4H), 1.64-2.06 (m, 6H).

Workup

  1. customThe solvent is removed in vacuo
  2. customthe residue is partitioned between water (10 mL) and EtOAc (20 mL)
  3. customThe layers are separated
  4. extractionthe aqueous layer is extracted with EtOAc (2×10 mL)
  5. customThe combined extracts are dried
  6. customevaporated
  7. customThe resulting oil is purified by PTLC with 100:5:0.5 DCM

Sources & evidence

ORD record
ord-4de12afa32cf4f2ba0aee6502a4ed2bf
Source dataset
uspto-grants-2010_09
Patent number
US07795262B2

Reaction notes

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