Triethylamine → HCID 57433670, compound

HRID 1783812Notes

Reaction equation

HRID 1783812 reaction equation
Cl.[F:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[C:11]3[N:15]([C:16]=2[C:17]2[CH:22]=[CH:21][N:20]=[C:19]([NH:23][CH:24]4[CH2:29][CH2:28][CH2:27][NH:26][CH2:25]4)[N:18]=2)[CH:14]=[CH:13][S:12]3)=[CH:5][CH:4]=1.C(N(CC)CC)C.[F:37][C:38]1[CH:45]=[CH:44][C:41]([CH:42]=O)=[CH:40][CH:39]=1.ClCCCl.CN(C=O)C>ClCCCl.CN(C=O)C>[F:37][C:38]1[CH:45]=[CH:44][C:41]([CH2:42][N:26]2[CH2:27][CH2:28][CH2:29][CH:24]([NH:23][C:19]3[N:18]=[C:17]([C:16]4[N:15]5[C:11]([S:12][CH:13]=[CH:14]5)=[N:10][C:9]=4[C:6]4[CH:7]=[CH:8][C:3]([F:2])=[CH:4][CH:5]=4)[CH:22]=[CH:21][N:20]=3)[CH2:25]2)=[CH:40][CH:39]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 680234-FluorobenzaldehydeHCID 20184825Dce dmfHCID 68796794HCID 68796794, compound

Product 1

HCID 57433670HCID 57433670, compoundYield 56.2%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6228DimethylformamideSolvent

Procedure

The racemic 4-[6-(4-fluorophenyl)imidazo[2,1-b][1,3]thiazol-5-yl]-N-[piperidin-3-yl]pyrimidin-2-amine hydrochloride (70 mg g, 0.15 mmol) was dissolved in a 80/20 mixture of DCE and DMF (1.2 ml) and treated with three equivalent of triethylamine (63 uL). The 4-fluorobenzaldehyde (19 mg, 0.15 mmol) was added, followed by a 0.2 M solution of Me4NBH(OAc)3 in 80/20 DCE/DMF (1.2 ml). The mixture was stirred at room temperature for 18 hours. The mixture was washed with a 1N sodium hydroxide solution (2 ml). Concentration in vacuo followed by purification on reverse phase HPLC provides the title compound as a pale yellow solid (42.4 mg, 56%). M.p.=131-133° C. 400 MHz 1H NMR (DMSO-d6) δ: 8.73 (br. s, 1H), 8.06 (d, J=5.1 Hz, 1H), 7.64-7.58 (m, 2H), 7.44 (d, J=4.7 Hz, 1H), 7.35-7.31 (m, 2H), 7.30-7.23 (m, 2H), 7.07 (t, J=8.8 Hz, 2H), 7.00 (br. s, 1H), 6.29 (d, J=5.1 Hz, 1H), 4.00-3.90 (m, 1H), 3.49 (s, 2H), 2.96-2.90 (m, 1H), 2.69-2.62 (m, 1H), 2.08-1.94 (m, 2H), 1.93-1.85 (m, 1H), 1.76-1.67 (m, 1H), 1.61-1.48 (m, 1H), 1.42-1.30 (m, 1H). LCMS: 503 [M+H].

Workup

  1. washThe mixture was washed with a 1N sodium hydroxide solution (2 ml)
  2. concentrationConcentration in vacuo
  3. customfollowed by purification on reverse phase HPLC

Sources & evidence

ORD record
ord-32a67e0def91432ab509dd4b57a85004
Source dataset
uspto-grants-2009_03
Patent number
US07501430B2

Reaction notes

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