1-Ethynylcyclohexanol → Gne-2861

HRID 1398674Notes

Reaction equation

[NH2:1][C:2]1[N:7]=[C:6]([N:8]2[C:12]3[CH:13]=[C:14](Br)[CH:15]=[CH:16][C:11]=3[N:10]=[C:9]2[NH:18][CH2:19][CH2:20][O:21][CH3:22])[CH:5]=[CH:4][N:3]=1.C(N(CC)CC)C.[C:30]([C:32]1([OH:38])[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]1)#[CH:31]>CS(C)=O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[NH2:1][C:2]1[N:7]=[C:6]([N:8]2[C:12]3[CH:13]=[C:14]([C:31]#[C:30][C:32]4([OH:38])[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]4)[CH:15]=[CH:16][C:11]=3[N:10]=[C:9]2[NH:18][CH2:19][CH2:20][O:21][CH3:22])[CH:5]=[CH:4][N:3]=1

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of 1-(2-aminopyrimidin-4-yl)-6-bromo-N-(2-methoxyethyl)-1H-1,3-benzodiazol-2-amine (150 mg, 0.39 mmol, 95%), triethylamine (2 mL), 1-ethynylcyclohexan-1-ol (300 mg, 2.42 mmol) and bis(triphenylphosphine)palladium(II) dichloride (300 mg, 0.43 mmol) in dimethylsulfoxide (3 mL) was stirred under nitrogen for 1 hr at 70° C. The reaction mixture was purified on a C18 column (acetonitrile/water, 5:95-80:20) to give 30 mg (19%) of 1-[2-[1-(2-aminopyrimidin-4-yl)-2-[(2-methoxyethyl)amino]-1H-1,3-benzodiazol-6-yl]ethynyl]cyclohexan-1-ol as a white solid: 1H NMR (300 MHz, DMSO) delta 8.43 (d, J=5.4 Hz, 1H), 8.22 (d, J=5.4 Hz, 1H), 7.50 (s, 1H), 7.30-7.10 (m, 4H), 6.91 (s, 1H), 5.33 (s, 1H), 4.69-4.55 (m, 4H), 3.30 (s, 3H), 1.90-1.20 (m, 10H); LC-MS: m/z=407 (M+H)+.

Workup

customThe reaction mixture was purified on a C18 column (acetonitrile/water, 5:95-80:20)

Sources & evidence

ORD record: ord-241824a1aa2e470c86681d3cb7e23f06
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08901313B2

Reaction notes

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