Ammonia → HCID 73053677, compound

HRID 1526505Notes

Reaction equation

HRID 1526505 reaction equation
[NH3:1].[N:2]1([CH:8]2[CH2:13][CH2:12][CH:11]([NH:14][C:15]3[C:16]4[C:17]5[C:22]([S:23][C:24]=4[N:25]=[CH:26][N:27]=3)=[CH:21][CH:20]=[C:19]([CH2:28][C:29]([O:31]CC)=O)[CH:18]=5)[CH2:10][CH2:9]2)[CH2:7][CH2:6][O:5][CH2:4][CH2:3]1>C(O)C>[N:2]1([CH:8]2[CH2:9][CH2:10][CH:11]([NH:14][C:15]3[C:16]4[C:17]5[C:22]([S:23][C:24]=4[N:25]=[CH:26][N:27]=3)=[CH:21][CH:20]=[C:19]([CH2:28][C:29]([NH2:1])=[O:31])[CH:18]=5)[CH2:12][CH2:13]2)[CH2:7][CH2:6][O:5][CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 73053665HCID 73053665, compound

Product 1

HCID 73053677HCID 73053677, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Into a saturated solution of ammonia (gas) in ethanol (50 mL) was added ethyl 2-(3-[[4-(morpholin-4-yl)cyclohexyl]amino]-8-thia-4,6-diazatricyclo[7.4.0.0 [2,7]]trideca-1(13),2(7),3,5,9,11-hexaen-12-yl)acetate (100 mg, 0.22 mmol, 1.00 equiv) and the resulting solution was sealed and stirred overnight at room temperature. After completion, the solvent was removed under reduced pressure. The residue was applied onto a silica gel column with dichloromethane/methanol/NH4OH (15:1:0.05) to provide the resulted 2-(3-[[4-(morpholin-4-yl)cyclohexyl]amino]-8-thia-4,6-diazatricyclo[7.4.0.0 [2,7]]trideca-1(13),2(7),3,5,9,11-hexaen-12-yl)acetamide (38.5 mg, 41%) as a off-white solid. LC/MS: (ES, m/z) 426 [M+H]+. 1H-NMR (400 MHz, CDCl3) δ 8.60 (s, 1H), 7.93-7.91 (d, 1H), 7.75 (s, 1H), 7.45-7.40 (t, 1H), 5.46-5.42 (d, 2H), 5.35-5.32 (d, 2H), 4.31-4.16 (m, 1H), 3.81-3.79 (m, 6H), 2.64-2.60 (d, 3H), 2.46-2.40 (d, 3H), 2.07-1.98 (m, 2H), 1.58-1.55 (m, 2H), 1.48-1.42 (m, 2H).

Workup

  1. customthe resulting solution was sealed
  2. customAfter completion, the solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-37f3722d93514a87a17cc60e312ad9e5
Source dataset
uspto-grants-2015_07
Patent number
US09085586B2

Reaction notes

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