Triethylamine → HCID 86695264, compound

HRID 1504103Notes

Reaction equation

HRID 1504103 reaction equation
Cl[C:2]1[N:3]=[CH:4][N:5]=[C:6]2[C:13]=1[C:12]1[C@@H:11]([CH2:14][OH:15])[CH2:10][CH2:9][C:8]=1[S:7]2.C(N(CC)CC)C.Cl.[N:24]1([CH:30]2[CH2:35][CH2:34][CH:33]([NH2:36])[CH2:32][CH2:31]2)[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1>CN(C=O)C.C(Cl)Cl>[N:24]1([CH:30]2[CH2:31][CH2:32][CH:33]([NH:36][C:2]3[N:3]=[CH:4][N:5]=[C:6]4[C:13]=3[C:12]3[C@@H:11]([CH2:14][OH:15])[CH2:10][CH2:9][C:8]=3[S:7]4)[CH2:34][CH2:35]2)[CH2:25][CH2:26][O:27][CH2:28][CH2:29]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 86695265HCID 86695265, compoundHCID 86695266HCID 86695266, compound

Product 1

HCID 86695264HCID 86695264, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

To a 100 mL round-bottom flask containing a solution of [(3S)-12-chloro-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(12),2(6),8,10-tetraen-3-yl]methanol (100 mg, 0.42 mmol, 1.00 equiv) in anhydrous DMF (8 mL) was added triethylamine (372 mg, 3.68 mmol, 9.00 equiv) and 4-(morpholin-4-yl)cyclohexan-1-amine hydrochloride (214 mg, 0.83 mmol, 2.00 equiv) at room temperature. The resulting solution was stirred overnight at 80° C. After cooling, the resulting solution was diluted with DCM (50 mL), washed with brine, dried over anhydrous sodium sulfate and concentrated under vacuum to obtain 130 mg (81%) of [(3S)-12-[[4-(morpholin-4-yl)cyclohexyl]amino]-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(12),2(6),8,10-tetraen-3-yl]methanol as a yellow oil. MS (ES): m/z 389 (M+H)+.

Workup

  1. temperatureAfter cooling
  2. washwashed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-4ed185548dca46d0996091828377c665
Source dataset
uspto-grants-2015_12
Patent number
US09212190B2

Reaction notes

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