Dichloromethane → N-methyl-4-[7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(12),2(6),8,10-tetraen-12-yloxy]cyclohexan-1-amine hydrochloride

HRID 2369433Notes

Reaction equation

HRID 2369433 reaction equation
[CH3:1][N:2]([CH:10]1[CH2:15][CH2:14][CH:13]([O:16][C:17]2[N:18]=[CH:19][N:20]=[C:21]3[C:28]=2[C:27]2[CH2:26][CH2:25][CH2:24][C:23]=2[S:22]3)[CH2:12][CH2:11]1)C(=O)OC(C)(C)C.[Cl:29]CCl>Cl>[ClH:29].[CH3:1][NH:2][CH:10]1[CH2:15][CH2:14][CH:13]([O:16][C:17]2[N:18]=[CH:19][N:20]=[C:21]3[C:28]=2[C:27]2[CH2:26][CH2:25][CH2:24][C:23]=2[S:22]3)[CH2:12][CH2:11]1

Participants

4

Reactant 2

HCID 6344DichloromethaneHCID 68110120tert-butyl N-methyl-N-(4-[7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(12),2(6),8,10-tetraen-12-yloxy]cyclohexyl)carbamate

Product 1

HCID 68109920N-methyl-4-[7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(12),2(6),8,10-tetraen-12-yloxy]cyclohexan-1-amine hydrochlorideYield 92%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Into a 100-mL round-bottom flask, was placed a solution of tert-butyl N-methyl-N-(4-[7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(12),2(6),8,10-tetraen-12-yloxy]cyclohexyl)carbamate (450 mg, 1.12 mmol, 1.00 equiv) in dichloromethane (50 mL), hydrochloric acid (1.0 mL, 12 M) was added and the resulting solution was stirred for 3 h at room temperature. The resulting mixture was concentrated under vacuum to provide N-methyl-4-[7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(12),2(6),8,10-tetraen-12-yloxy]cyclohexan-1-amine hydrochloride (350 mg 92%) as a white solid.

Workup

  1. customInto a 100-mL round-bottom flask, was placed
  2. concentrationThe resulting mixture was concentrated under vacuum

Sources & evidence

ORD record
ord-07033d71070844efaf038051126ee8d8
Source dataset
uspto-grants-2014_04
Patent number
US08703941B2

Reaction notes

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