Ammonia → HCID 86695215, compound

HRID 1504057Notes

Reaction equation

HRID 1504057 reaction equation
[NH3:1].[CH3:2][N:3]([CH:11]1[CH2:16][CH2:15][CH:14]([O:17][C:18]2[C:29]3[C:28]4[C@@H:27]([CH2:30][CH:31]=O)[CH2:26][CH2:25][C:24]=4[S:23][C:22]=3[N:21]=[CH:20][N:19]=2)[CH2:13][CH2:12]1)[C:4](=[O:10])[O:5][C:6]([CH3:9])([CH3:8])[CH3:7].[C-:33]#[N:34].[Na+].[NH4+].[Cl-]>CO>[NH2:1][CH:31]([C:33]#[N:34])[CH2:30][C@H:27]1[CH2:26][CH2:25][C:24]2[S:23][C:22]3[N:21]=[CH:20][N:19]=[C:18]([O:17][CH:14]4[CH2:15][CH2:16][CH:11]([N:3]([CH3:2])[C:4](=[O:10])[O:5][C:6]([CH3:9])([CH3:7])[CH3:8])[CH2:12][CH2:13]4)[C:29]=3[C:28]1=2

Participants

6

Reactant 4

HCID 222AmmoniaHCID 8929Sodium CyanideHCID 25517Ammonium ChlorideHCID 86695117HCID 86695117, compound

Product 1

HCID 86695215HCID 86695215, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Ammonia gas was introduced in 50 mL of CH3OH at 5° C. for 15 min. To the above solution was added tert-butyl N-methyl-N-(4-[[(3R)-3-(2-oxoethyl)-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(8),2(6),9,11-tetraen-12-yl]oxy]cyclohexyl)carbamate (700 mg, 1.57 mmol, 1.00 equiv), NaCN (93.1 mg, 1.90 mmol, 1.20 equiv) and NH4Cl (92.5 mg, 1.73 mmol, 1.10 equiv) successively. The resulting mixture was stirred for 16 h at room temperature and concentrated under reduced pressure. The residue was applied onto a silica gel column with dichloromethane/methanol (1:30) to afford tert-butyl N-(4-[[(3R)-3-(2-amino-2-cyanoethyl)-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(8),2(6),9,11-tetraen-12-yl]oxy]cyclohexyl)-N-methylcarbamate (600 mg, 81%) as a yellow oil.

Workup

  1. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-207a2f50ef9f4feea0134ec2c11985c1
Source dataset
uspto-grants-2015_12
Patent number
US09212190B2

Reaction notes

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