Hydrochloric Acid → HCID 86695108, compound

HRID 1503930Notes

Reaction equation

HRID 1503930 reaction equation
[CH3:1][N:2]([CH:10]1[CH2:15][CH2:14][CH:13]([O:16][C:17]2[C:28]3[C:27]4[C@@H:26]([CH2:29][CH2:30][C:31]5[O:32][CH:33]=[CH:34][N:35]=5)[CH2:25][CH2:24][C:23]=4[S:22][C:21]=3[N:20]=[CH:19][N:18]=2)[CH2:12][CH2:11]1)C(=O)OC(C)(C)C.Cl>ClCCl>[CH3:1][NH:2][CH:10]1[CH2:11][CH2:12][CH:13]([O:16][C:17]2[C:28]3[C:27]4[C@@H:26]([CH2:29][CH2:30][C:31]5[O:32][CH:33]=[CH:34][N:35]=5)[CH2:25][CH2:24][C:23]=4[S:22][C:21]=3[N:20]=[CH:19][N:18]=2)[CH2:14][CH2:15]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86695106HCID 86695106, compound

Product 1

HCID 86695108HCID 86695108, compoundYield 91.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl N-methyl-N-(4-[[(3S)-3-[2-(1,3-oxazol-2-yl)ethyl]-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(8),2(6),9,11-tetraen-12-yl]oxy]cyclohexyl)carbamate (110 mg, 0.22 mmol, 1.00 equiv) in dichloromethane (5 mL) was added hydrogen chloride (12 M, 1 mL) at 0° C. and the resulting mixture was stirred at room temperature for 2 h. The reaction mixture was concentrated under reduced pressure and the residue was neutralized with sodium hydroxide and extracted with 2×30 mL of dichloromethane. The combine organic layers were concentrated in vacuo to give N-methyl-4-[[(3S)-3-[2-(1,3-oxazol-2-yl)ethyl]-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(8),2(6),9,11-tetraen-12-yl]oxy]cyclohexan-1-amine (80 mg, crude) as a yellow oil.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. extractionextracted with 2×30 mL of dichloromethane
  3. concentrationThe combine organic layers were concentrated in vacuo

Sources & evidence

ORD record
ord-643163b89b46452e8f10314844a5f747
Source dataset
uspto-grants-2015_12
Patent number
US09212190B2

Reaction notes

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