Pyridine → HCID 22000386, compound

HRID 917495Notes

Reaction equation

HRID 917495 reaction equation
[NH2:1][CH2:2][C@H:3]1[CH2:8][CH2:7][C@H:6]([NH:9][C:10]2[S:11][C:12]3[CH2:19][CH2:18][CH2:17][C:16]4[CH:20]=[CH:21][C:22]([F:24])=[CH:23][C:15]=4[C:13]=3[N:14]=2)[CH2:5][CH2:4]1.N1C=CC=CC=1.C(N(C(C)C)CC)(C)C.Cl[C:41]([O:43][CH2:44][CH2:45][Cl:46])=[O:42]>O>[Cl:46][CH2:45][CH2:44][O:43][C:41](=[O:42])[NH:1][CH2:2][CH:3]1[CH2:8][CH2:7][CH:6]([NH:9][C:10]2[S:11][C:12]3[CH2:19][CH2:18][CH2:17][C:16]4[CH:20]=[CH:21][C:22]([F:24])=[CH:23][C:15]=4[C:13]=3[N:14]=2)[CH2:5][CH2:4]1

Participants

6

Reactant 4

HCID 1049PyridineHCID 123052-Chloroethyl chloroformateHCID 81531DiisopropylethylamineHCID 178511277HCID 178511277, compound

Product 1

HCID 22000386HCID 22000386, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of trans-N2-[4-(aminomethyl)cyclohexyl]-9-fluoro-5,6-dihydro-4H-benzo-[6,7]cyclohepta[d][1,3]thiazol-2-amine (5.00 g, 11.95 mmol), 20 ml anhydrous pyridine, and 8 ml diisopropylethylamine was stirred under N2. Then 2-chloroethyl chloroformate (1.40 ml, 13.6 mmol) was added dropwise to the stirring solution. The solution was stirred at room temperature for 2 hours and then poured into 250 ml water and extracted with 250 ml EtOAc. The extract was separated and evaporated to yield 100% (5.40 g) of the desired product as a highly viscous golden oil: 1H-NMR (CDCl3) δ 1.13 (3H, m), 1.43 (1H, m), 1.82 (2H, m), 2.06 (2H, m), 2.22 (2H, m), 2.81 (4H, m), 3.06 (2H, t, J=6.4 Hz), 3.25 (1H, m), 3.70 (3H, m), 4.31 (2H, t, J=5.7 Hz), 4.89 (2H, m), 6.82 (1H, t, J=2.8 Hz), 7.04 (1H, m), 7.70 (1H, dd, J=2.7, 10.8 Hz); 452 (ESMS, MH+).

Workup

  1. extractionextracted with 250 ml EtOAc
  2. customThe extract was separated
  3. customevaporated

Sources & evidence

ORD record
ord-31ad96e69a5d4d7aa636eb36c0a6f0fc
Source dataset
uspto-grants-2007_09
Patent number
US07273880B2

Reaction notes

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