Ethanol → HCID 178521598, compound

HRID 715638Notes

Reaction equation

HRID 715638 reaction equation
[NH2:1][C:2]1[C:3]([NH:16][CH:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)=[N:4][C:5]([NH:8][C@H:9]2[CH2:14][CH2:13][C@H:12]([OH:15])[CH2:11][CH2:10]2)=[N:6][CH:7]=1.[F:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[C:24]=1[N:30]=[C:31]=S.C(O)C.CC(N=C=NC(C)C)C>CN(C=O)C>[F:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[C:24]=1[NH:30][C:31]1[N:16]([CH:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)[C:3]2[C:2]([N:1]=1)=[CH:7][N:6]=[C:5]([NH:8][C@H:9]1[CH2:10][CH2:11][C@H:12]([OH:15])[CH2:13][CH2:14]1)[N:4]=2

Participants

6

Reactant 4

HCID 702EthanolHCID 12734DiisopropylcarbodiimideHCID 40316012,6-Difluorophenyl isothiocyanateHCID 178508036HCID 178508036, compound

Product 1

HCID 178521598HCID 178521598, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-{[5-Amino-4-(cyclopentylamino)pyrimidin-2-yl]amino}trans-cyclohexan-1-ol (1.13 mmol, 330 mg) was dissolved in DMF (8.5 mL) and 2,6-difluorophenyl-isothiocyanate (1.13 mmol, 0.146 mL) was added. The reaction mixture was stirred at room temperature for about 90 minutes. Ethanol (2.5 mL) was added and the reaction mixture was stirred for about an additional 30 minutes. N,N-Diisopropylcarbodiimide (3.40 mmol, 0.532 mL) was added and the reaction mixture was stirred overnight. Solvent was removed and the residue was purified using column chromatography (SiO2, 1:1 n-hexanes/ethyl acetate→ethyl acetate→1% methanol/ethyl acetate) to give the desired product (222.5 mg, 46% yield). ES-MS: 429 (M+1). Tetrahydrofuran can also be used as solvent in this step.

Workup

  1. stirringthe reaction mixture was stirred for about an additional 30 minutes
  2. stirringthe reaction mixture was stirred overnight
  3. customSolvent was removed
  4. customthe residue was purified

Sources & evidence

ORD record
ord-3d7e7d7a7bf34190971fd72b01935e6c
Source dataset
uspto-grants-2015_11
Patent number
US09187479B2

Reaction notes

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