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Diisopropylethylamine → 4-(((1R,4S)-4-Hydroxy-3,3-dimethylcyclohexyl)amino)-2-((2-(2-oxo-2,3-dihydro-1H-benzo[d]imidazol-1-yl)ethyl)amino)pyrimidine-5-carbonitrile

HRID 1749511
Notes
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Reaction equation

HRID 1749511 reaction equation
[OH:1][C@H:2]1[CH2:7][CH2:6][C@@H:5]([NH:8][C:9]2[C:14]([C:15]#[N:16])=[CH:13][N:12]=[C:11](S(C)(=O)=O)[N:10]=2)[CH2:4][C:3]1([CH3:22])[CH3:21].[NH2:23][CH2:24][CH2:25][N:26]1[C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=2[N:28](C)[C:27]1=[O:36].CCN(C(C)C)C(C)C>C1COCC1>[OH:1][C@H:2]1[CH2:7][CH2:6][C@@H:5]([NH:8][C:9]2[C:14]([C:15]#[N:16])=[CH:13][N:12]=[C:11]([NH:23][CH2:24][CH2:25][N:26]3[C:30]4[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=4[NH:28][C:27]3=[O:36])[N:10]=2)[CH2:4][C:3]1([CH3:22])[CH3:21]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 289166861-(2-Amino-ethyl)-3-methyl-1,3-dihydro-benzoimidazol-2-oneHCID 1181621034-(((1R,4S)-4-hydroxy-3,3-dimethylcyclohexyl)amino)-2-(methylsulfonyl)pyrimidine-5-carbonitrile

Product 1

HCID 1181794234-(((1R,4S)-4-Hydroxy-3,3-dimethylcyclohexyl)amino)-2-((2-(2-oxo-2,3-dihydro-1H-benzo[d]imidazol-1-yl)ethyl)amino)pyrimidine-5-carbonitrileYield 27.3%

Reagents, catalysts & solvents

1
HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4-(((1R,4S)-4-hydroxy-3,3-dimethylcyclohexyl)amino)-2-(methylsulfonyl)pyrimidine-5-carbonitrile (100 mg, 0.308 mmol), 1-(2-amino-ethyl)-3-methyl-1,3-dihydro-benzoimidazol-2-one (140 mg, crude), and DIEA (85 mg, 0.66 mmol) in THF (3 mL) was stirred at 100° C. in a microwave reactor for 1.5 h. After cooling to room temperature, the reaction mixture was concentrated and the residue was purified by preparative standard methods to afford the title compound (36.7 mg, 0.084 mmol, 24% yield over 2 steps). 1H NMR (400 MHz, CD3OD) δ (ppm) 8.08-7.94 (m, 1H), 7.11-7.08 (m, 4H), 4.26-4.10 (m, 3H), 3.89-3.66 (m, 2H), 3.40-3.35 (m, 4H), 1.96-1.51 (m, 6H), 1.05-0.99 (m, 6H). MS (ESI) m/z 436.2 [M+H]+.

Workup

  1. temperatureAfter cooling to room temperature
  2. concentrationthe reaction mixture was concentrated
  3. customthe residue was purified by preparative standard methods

Sources & evidence

ORD record
ord-efbf391893d24502a7311d48d79c21a5
Source dataset
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09156798B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes