HCID 178453641, compound → HCID 178511277, compound

HRID 1976125Notes

Reaction equation

HRID 1976125 reaction equation
[F:1][C:2]1[CH:31]=[CH:30][C:5]2[CH2:6][CH2:7][CH2:8][C:9]3[S:13][C:12]([NH:14][C@H:15]4[CH2:20][CH2:19][C@H:18]([CH2:21][NH:22]C(=O)OC(C)(C)C)[CH2:17][CH2:16]4)=[N:11][C:10]=3[C:4]=2[CH:3]=1>CCOC(C)=O.Cl.O1CCOCC1>[NH2:22][CH2:21][C@H:18]1[CH2:19][CH2:20][C@H:15]([NH:14][C:12]2[S:13][C:9]3[CH2:8][CH2:7][CH2:6][C:5]4[CH:30]=[CH:31][C:2]([F:1])=[CH:3][C:4]=4[C:10]=3[N:11]=2)[CH2:16][CH2:17]1

Participants

5

Reactant 1

HCID 178453641HCID 178453641, compound

Product 1

HCID 178511277HCID 178511277, compoundYield 97.4%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of trans-tert-butyl N-({4-[(9-fluoro-5,6-dihydro-4H-benzo[6,7]cyclohepta[d][1,3]thiazol-2-yl)amino]cyclohexyl}-methyl)carbamate (34.5 g, 77.0 mmol) in 200 ml EtOAc and 100 ml 4N HCl in dioxane was stirred at room temperature for 2 hours. The resulting solid was collected by filtration and the solid product washed with Et2O and dried under vacuum to yield 25.9 g of the desired product as a pale yellow solid. An additional 1.43 g of the product was obtained by allowing the filtrate to stand in a closed flask for several days. The overall yield was 85%: 1H-NMR (CD3OD) δ 1.25 (2H, m), 1.51 (2H, m), 1.70 (1H, broad), 1.95 (2H, m), 2.18 (4H, m), 2.80 (6H, m), 3.63 (1H, broad), 7.11 (1H, dt, J=2.5 Hz, 8.4 Hz), 7.36 (2H, m); 346 (ESMS, MH+).

Workup

  1. filtrationThe resulting solid was collected by filtration
  2. washthe solid product washed with Et2O
  3. customdried under vacuum

Sources & evidence

ORD record
ord-c2977cf48e774dacad4a487a7306ca9c
Source dataset
uspto-grants-2001_05
Patent number
US06225330B1

Reaction notes

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